Versions of method of producing derivatives of 4-acetoxy-3-oxyethyl-azetidi-2-non

专利摘要:
A process for preparing 4-acetoxy-3-hydroxyethyl- azetizin-2-one derivative having the general formula (II): wherein R' is a protective group for hydroxy group, which comprises reacting the β-lactam compound having the general formula (I): wherein R' is above, R2, R3 and R4 are a lower alkyl group of C, to C4, phenyl group or aralkyl group and R is a protective group for N, with acetic anhydride in the organic solvent in the presence of base and then removing the protective group for N. 4-Acetoxy-3-hydroxyethylazetizin-2-one derivatives are the useful intermediates for preparing carbapenem β-lactam antibiotics such as thienamycin and penem β-lactam antibiotics.
公开号:SU1442071A3
申请号:SU853923699
申请日:1985-07-03
公开日:1988-11-30
发明作者:Охаси Такехиса；Кан Казунори；Сада Исао；Мияма Акимаса；Ватанабе Киеси
申请人:Канегафути Кагаку Когио Кабусики Кайся (Фирма)；
IPC主号:

专利说明:

 Oj
11442071
This invention relates to the preparation of novel 4-acetoxy-3-hydroxy-ethylazetidin-2-one derivatives of the general formula
ORj
i with
CHj-CH- 0
ososn
NH
where Ry, is a trialkylsilyl group, which are intermediates in the synthesis of Carbocene B-lactam antibiotics.
The aim of the invention is to develop, on the basis of the known techniques, a method for the preparation of novel intermediates for the synthesis of carbocene b-lactam antibiotics, which
raw product. This liquid product is purified by separation in a chromatographic column with
silica gel (eluted with benzene-hexane in a 2: 1 ratio) and the result is 0.5 g (3K, 4R, 5R) -4-acetoxy-1- (tert-butyldimethylsnlyl) -3- (1-tert -boots1Dimethylsilyloxyethyl) -azetidin-2-it in the form of a liquid.
This liquid product in an amount of 0.5 g is introduced into 2 ml of tetrahydrofuran, where g of tetrabutylammonium fluoride and 0.17 g of acetic acid are introduced into 2 ml of tetrahydrofuran solution and the mixture is stirred for 30 minutes at room temperature. After entering into the reaction
20 ml of ethyl acetate can be obtained in a much simpler 20% mixture.
and with high yields.
EXAMPLE 1 Preparation of (3R, 4R) -4-acetoxy-3- (R) -1-tert-byte-Idimethylyl-xyloxythyl-azetid-2-one.
1.0 g of (3R, 5R) -3- (1-TpeT-6yTmj-dimethylsilyloxyethyl) -4-trimetesh1-lilyloxyazetidin-2-one is dissolved in 10 MP of dimethylformamide, where 0.89 g of triethylamine and g of tertwol are added. tildimethylsilyl chloride and the mixture is stirred for 9 hours at room temperature. After termination of the reaction, dimethylformamide is distilled off under reduced pressure, and dimethylformamide is added to under a reduced pressure and 30 ml is added. hexane. Thereafter, the solution is washed successively with a 2.5% aqueous solution of NaHCO, an aqueous solution of hydrochloric acid with a pH value of 3 and a saturated solution of salt, and dried with magnesium sulfate, the solvent is distilled off and a resultant of 1.24 g of a liquid substance is obtained. raw product.
1.0 g of this liquid product is added to 5 ml of methylene chloride, then 0.85 g of dimethylaminopyridine and 1.1 ml of acetic anhydride are added and the mixture is reacted for 6 hours at room temperature. The reaction mixture is then successively washed with a 5% aqueous solution of NaHCOi, an aqueous solution of hydrochloric acid with a pH value of 3 and a saturated solution of salt, and dried with magnesium sulfate, the solvent is distilled off and as a result, 0.8 g of a liquid substance is obtained,
five
0
- d 15
The aqueous solution is washed successively with a 5% NaHCQa aqueous solution.
tf
and brine and dried over magnesium sulfate. The solvent is distilled off and as a result 0.30 g of the desired compound is obtained as a crystalline substance. The resulting crystalline substance is purified on a silica gel column chromatography (with a mixture of benzene and ethyl acetate 6: 1) and 0.27 g of the desired B-lactam is obtained as a solid. M.p. 107-108 C,
solids, Cii (d + 50 ° (C 0.5 CHCl: i).
 NNRM (90 MHz, CDCl) ff
0
five
LfllGKTpiiJLl lL J i ll D j U L -X
Ppm: 0.08 (6H, s); 0.84 (9H, c) j 1.20 (3H,) i 2.01 (3H, O 3.04 (1H,}); 4.12 (1H, M); 5.76 (1H,); 6.73 (NH).
Example 2. Preparation of (3R, 4R) -4-acetoxy-3-t (R) -1-tert-by-dimethylsilyloxyethyl} -azetidin-2-one.
1 g of (ZRJ4R) -1-tert-butylmethylsil-3-CU-1-tert-butyldimethylsilyloxyethyl-4-trimethyl-1-Lloxyazetidin-2- is dissolved in 10 ml of methyl methylene chloride, 0.85 g of di-chloride is added to the solution. methylaminopyridine and 0.71 g of acetic anhydride, and the mixture reacts for one day at 0 ° C. The reaction mixture is then diluted with hexane and washed successively with a 5% aqueous solution of NaHCOj, aqueous soluble hydrochloric acid with a pH of 4 and a saturated solution salt, the resulting product is dried with magnesium sulfate and the solvent is distilled off, as a result of 7H), 0.85 g of liquid P11 P11 is obtained (schukta).
The resulting liquid substance is purified on a chromatographic column with silica gel (eluted with a mixture of hexane-ether in a ratio of 30: 1), resulting in 0.40 g (3R, 4K). 4-acetoxy-1-tert. -bootsh1Di- methylsilyl-3- (K) -1-tert-butyldimethylsilyloxyethane1 azetidin-2-one as a colorless liquid,
Into the resulting liquid product, 2 htn t ether and hydrofura are introduced, then 0.26 g of tetrabutylamnoni fluoride and 0.12 g of acetic acid in 2 MP of tetrahydrofuran are introduced into the solution, and the mixture is stirred for 30 minutes at room temperature. After adding 20 ml of ethyl acetate to the reaction mixture, this mixture is washed sequentially with a 5% aqueous solution of NaHCO 3. and brine and dried over magnesium sulfate. The solvent is distilled off, whereby 0.29 g of a solid is obtained. The resulting solid is recrystallized from hexane and as a result 0.20 g of the desired lactam is obtained in the form of colorless needles.
The properties of the obtained In-lactam close to the properties specified in example 1.
Example 3, Preparation of (3R, 4R) -4-acetoxy-3- (K) -1-tert-butyl-dimethylsilyloxyethylazetizin-2-one.
1 g of (WE, 4K) -1-tert-butnyl dimethylsilyl-C 1 (K) -1-tert-botshvdimesh1ylyl-hydroxyethyl} -4-trimethylsilyloxy-azethyl-2-one is dissolved in 10 ml of chloro-dimethylsilyl) -3- G (R) -1-tert-butyl methylmethylIloxyethyl azetidin-2-one as a liquid.
The resulting liquid product is dissolved in 2 ml of tetrahydrofuran, 0.38 g of tetrabutylammonium fluoride and 0.17 g of acetic acid in 2 ml of tetrahydrofuran are introduced into the solution, the mixture
10 is stirred for 30 minutes at room temperature. After adding 20 ml of ethyl acetate to the reaction mixture, this reaction mixture is washed with a successive 5% aqueous solution.
15 with a solution of NaHCOj and a saturated solution of ol and dried over magnesium sulfate. The solvent is distilled off, resulting in a yield of 0.42 g of solid. The resulting solid 20 The doy is purified on a silica gel chromatography column (eluted with a mixture of hexane and ethyl ether in a ratio of 10: 3), resulting in a yield of 0.39 g
25 desired B-lactam in the form of colorless needles.
The properties of the y-lactam obtained are close to those indicated in Example 1.
30 Example 4. Preparation of (3R, 4R) -4-acetoxy-3-i (R) -1-isopropyl methylsilyloxyethyl-azetidin-2-one. 1.2 g of 3- (R) -1- and 3 opd opyldimethylsilyloxyethylZ-4-trimethylssh1yloxy35 azeti1scin-2-one (ЗR, 4R, 5R) -forma: (3 48,58) -form 5: 1) solution in 12 ml of dimethylformamide, 0.52 g of triatilamine and 0.7 of tert-butyldimethylsilyl chloride and
0.85 40 is added to the solution; the mixture is stirred for 9 h.
dimethylaminopyridine, 0.75 g of 2,6-lutidine and 1.42 g of acetic anhydride and the mixture is reacted for 44 hours at a temperature of -. The reaction mixture is then diluted with ether and washed successively with 5% aqueous, NaHCOj solution, aqueous hydrochloric acid solution with a pH value of 4 and all of the saline solution, and the resulting product is dried over magnesium sulfate. The solvent is distilled off and, as a result, 0.88 g of liquid crude product is obtained. The resulting liquid product is purified on a silica gel chromatography column (eluted with a mixture of hexane-ethyl acetate in a ratio of 100: 1), and the result is 0.58 g (3R, 4R) -4-aneTOKK-TpeT6yTHn-
at room temperature. After the reaction has stopped, the dnmethylformamide is distilled off under reduced pressure and 30 ml of hexane is added to the solution. Then the reaction mixture is washed successively with a 2.5% aqueous solution of NaHCOj, an aqueous solution of hydrochloric acid with a pH value and a saturated solution of salt is dried over magnesium sulfate, the solvent is distilled off, with the result that 1.13 g of a liquid crude product is obtained.
0.90 g of the resulting liquid product
gg of that is introduced into 10 mp of methylene chloride, 0.79 g of dimethylaminopyridine and 0.61 ml of acetic anhydride are introduced into the solution and the mixture is reacted for 16 hours at 4 ° C. Then
50
dimethylsilyl) -3-G (R) -1-tert-butyldimethyl-iloxyethyl azetidin-2-one as a liquid.
The liquid product obtained is dissolved in 2 ml of tetrahydrofuran, 0.38 g of tetrabutylammonium fluoride and 0.17 g of acetic acid are introduced into the solution in 2 ml of tetrahydrofuran, a mixture of
stirred for 30 minutes at room temperature. After adding 20 ml of ethyl acetate to the reaction mixture, this reaction mixture is washed successively with a 5% aqueous solution of NaHCOj and a saturated solution with an olium, and dried with magnesium sulfate. The solvent is distilled off, resulting in a yield of 0.42 g of solid. The solid obtained is purified in a chromatographic column with silica gel (eluted with a mixture of hexane and ether) in a ratio of 10: 3), resulting in a yield of 0.39 g
the desired B-lactam in the form of colorless needles.
The properties of the obtained y-lactam are close to the properties indicated in example 1.
Example 4. Preparation of (3R, 4R) -4-acetoxy-3-i (R) -1-isopropyldimethylsilyloxyethyl-azetidin-2-one. 1.2 g of 3- (R) -1- and 3 opd opyldimethylsilyloxyethylZ-4-trimethylsylloxyazet1-2-one (ЗR, 4R, 5R) -forma: (3S, 48.58) -form 5: 1) solution in 12 ml of dimethylformamide, 0.52 g of triatylamine and 0.79 g of tert-butyldimethylsilyl chloride and
at room temperature. After termination of the reaction, the dnmethylformamide is distilled off under reduced pressure and 30 ml of hexane is added to the solution. The reaction mixture is then washed successively with a 2.5% aqueous solution of NaHCOj, an aqueous solution of hydrochloric acid with a pH value of 5 and a saturated solution of salt is dried over magnesium sulfate, and the solvent is distilled off, resulting in 1.13 g of a liquid crude product.
0.90 g of the obtained liquid product is introduced into 10 ml of methylene chloride, 0.79 g of dimethylaminopyridine and 0.61 ml of acetic anhydride are introduced into the solution and the mixture is reacted for 16 hours at 4 ° C. Then
0
514
the reaction mixture is washed successively with a 5% aqueous solution of NaHCOj, an aqueous solution of hydrochloric acid with a pH value of 5 and a saturated solution of salt, dried with magnesium sulfate, the solvent is distilled off, and the result is 0.70 g of liquid cbiporo product. The resulting liquid product is purified on a silica gel chromatography column (eluted with a mixture of hexane-ether in a ratio of 100: 3), resulting in 0.20 g (4-acetoxy-1-tr, -butyldimethyl silyl) -3- (1 -isopropyl dimethylsilyloxyethyl) azetidin-2-it in the form of a liquid.
. 0.20 g of liquid cushion is introduced into 2 ml of tetrahydrofuran, 0.13 g of tetrabutylammonium fluoride and 0.03 g of acetic acid in 2 ml of tetrahydrofuran are introduced into this solution, and the mixture is stirred for 30 minutes at room temperature. In response


The procedure of Example 4 was repeated, except that instead of 3-G (R) -1-isopropyl methyl ethyl-ethyl-ethyl-4-trimethylsilyloxyazetidin-2-one (3R, 4R, 5R) -form (35,48,58) -form 5: 1) 1.2 g (3R, -4R, 5R) -3oic mixture was used; 60 mp-ethyl acetate- were introduced; 25
this mixture is washed successively; (1-isopropsh1Dimethylsil1-oxyethyl) -4- with 5% aqueous solution of NaHCO-trimetsh1Sh1yloxyazetidin-2-one, and with a saturated solution of salt and vys-instead of 0.79 g of dimethylaminopyridia
Googled with iagni sulfate. Dissolve 1.3 g of 4-piperidinopyridine
the body is distilled off as a result of the semi-. 30 and 0.5 g of the desired B-lactate 0.14 g of the desired crude product as a solid, that (3R, 4R, 5R) -form: (ЗR54R 5S) -opop Example 8, Preparation (3R, 4R) 4-acetoxy-3 (R) -1-dimethyl-1,1,2-t-methylpropylsilyloxy (ethyl) azetradine-D, 58 g (ЗR, 4R55R) form of this prodc 2-one 1. Duct in the form of white crystals. . .Dissolved 0.98 g (3R, 4R) -3 (1-) NML spectrum (90 MHz, CDClj (3Rdimes1-1,1,2-trimetsh1Propylstiloxy,
4R, 5R) -forma (f, ppm: 0.04 (6H, s); (eth1) -4-trimethylsilyloxyazetidin0, 90 (7H) - 1.23 (ZN,), 2.06 (ZN, c)}. -one in 5 ml of methipenchloride, added 3.13 (1H, 5d), 4.13 (1H, m) g 5.76 (1H, 40 are 0.58 g of triethylamine and 0.66 g of dima 5: 1), after recrystallization of the product from hexane, it is obtained
) 5b, 40 (NH) ..,
M.p. 92-94 ° C. , 2 (, 5, СНС1з).
Example 5. Preparation of (3R, 4R) 4-acetoxy-3- (R) -1-tert-butyldimethyl-silyloxyethyl-azetidin-2-one,
The example was carried out analogously to example 2 except that the solvents shown in the table were used.
methyl 1,1,1,2-trimethylpropylsilyl chloride and the mixture is stirred for 9 hours at room temperature. After completion of the reaction, the resultant
45 the mixture is washed with an aqueous solution of hydrochloric acid with a pH of 4, the solvent is distilled off under reduced pressure and obtain 1.28 g of liquid crude product. 1.27 g of the resulting liquid are added to 6 mp of methyl chloride, then 0.95 g of dimethylaminopyridine and 1.59 g of acetic anhydride are added and the mixture is reacted for 46 hours at
PRI me R 6. Preparation of (3R, 4R) - 4 acetoxy-3- (K) -1-tert-butyldimrtil-silyloxyethyl-azetidin-2-one.
The procedure of Example 2 was repeated, except that instead of (ZL. 4E) -1-tert-butyldimethylsilyl-3- (U 1 tert-butyldimethylsiloxyethyl-4-trimethylsilyloxyazetidin-2-she was used 1 g (3R, 4R, 5K) - 3- (1-tert-butyldimethylsilyl-Oxyethyl) -4-trimethylsyl-1oxyazetidin-2-one, and instead of 0.85 t of dimethylaminopyridine, 1.2 g of 4-pyrrole-Zdinopyridine was used and 0.25 g of the desired B-lactam was obtained as Tafepftoro substance.
Example 7. Preparation of (3R, 4R) -4-acetoxy-3 (K) -1-isopropyl dimethylsilyloxyethyl} -azetidin-2-one.
The procedure of Example 4 was repeated, except that instead of 3-G (R) -1-isopropyl methyl ethyl-ethyl-ethyl-4-trimethylsilyloxyazetidin-2-one (3R, 4R, 5R) -form (35,48,58) -form 5: 1) 1.2 g (3R, -4R, 5R) -3 are used
methyl 1,1,1,2-trimethylpropylsilyl chloride and the mixture is stirred for 9 hours at room temperature. After completion of the reaction, the resultant
the mixture is washed with an aqueous solution of hydrochloric acid with a pH of 4, the solvent is distilled off under reduced pressure and obtain 1.28 g of liquid crude product. 1.27 g of the obtained liquid are added to 6 mp of methyl chloride, then 0.95 g of dimethylaminopyridine and 1.59 g of acetic anhydride are added and the mixture is reacted for 46 hours at
-15 ° C. After washing the solution with a 5% aqueous solution of NaHCO and then with water, the organic layer is separated: the solvent is distilled off under reduced pressure and 1.27 g of liquid are obtained.
th raw product. 1.19 g of the obtained liquid is dissolved in 6 kp of methylene chloride, 0.6 g of tetramethyl ammonium chloride and 0.3 g of potassium fluoride and 0.68 g of acetic acid are added and stirring is carried out for 2 hours at room temperature. . After completion of the reaction, the resulting mixture is washed with a 5% aqueous solution of NaHCO3 and then with water, the organic layer is separated, condensed under reduced pressure, and 0.7 g of solid crude product is obtained. The resulting solid is then recrystallized from hexane and 0.35 g of the desired B-lactam is obtained as a solid.
The resulting B-lactam has the following properties.
M.p. eO-SI C. +41.6 (C 0.5 CHCl);
H-NMR spectrum (90 MHz, CDCl1), ppm: 0.8 (6H, s); 0.65 (6H, s) J 0.75 (bN, d); 1.15 (ZN, d), 1.40 (1H, m), 2.08 (ZN, s) i 3.00 (1H, dd); 4.10 (1H, M) i 5.71 (1H, d), 6.60 (NH)

权利要求:
Claims (2)
[1]
1. A method for preparing 4-acetoxy-3-hydroxyethyl-azetidin-2-one derivatives of the general formula ORi
ABOUT
OOSNz
in
Where. R ;, - the trial is kilyl, differing in that the compound of the general formula
ORi
CH I I Q $ i-R3 .Л-NH О
.-AT
.
where R, R and R are lower alkyl, are reacted with a compound of the general Formula
X - R
d)
where X is halogen;
RJ - is a protecting group for nitrogen,
such as trialkylsilyl formed with the unity of the general formula
f
-T-OSi-Rj N-Rc R
CHg-CH- 0
five
where R, -Rj - have the indicated values are treated with acetic anhydride in an organic solvent medium in the presence of a base with the following removal of the nitrogen protective group.
[2]
2. A method for preparing 4-acetoxy-3-oxystilasetidin-2-one derivatives of the general formula
ORi SNZ-CH-p-GOSOSNz
lnh
where R, is a trialkyl group, characterized in that 0 is a compound of the general formula
.R,
I
СНзСН
-pOSi-Кз NBs R4
R.i, R3 R
5 0 where R - has the indicated values i and
- lower alkyl; RS is a nitrogen protecting group, such as trialkylsilyl,
treated with acetic anhydride in organic solvent in the presence of a base, followed by removal of the protective group 5 for nitrogen.
Priority n
a m: 07/05/84 - with R
p p and 3 n a-
I
tert-butyldimethylsilyl
01/14/85 - with R, - isopropyl dimethylsilyl.

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引用文献:

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公开号 | 申请日 | 公开日 | 申请人 | 专利标题

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US4861877A|1984-07-05|1989-08-29|Kanegafuchi Kagaku Kogyo Kabushiki Kaisha|Process for preparing 4-acetoxy-3-hydroxyethylazetidin-2-one derivatives|

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US4791198A|1984-07-05|1988-12-13|Kanegafuchi Kagaku Kogyo Kabushiki Kaisha|Beta-lactam compound and preparation thereof|

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JPS62164689A|1986-01-14|1987-07-21|Kanegafuchi Chem Ind Co Ltd|Novel beta-lactam compound and production thereof|

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EP0234484B1|1986-02-19|1993-10-20|Sanraku Incorporated|Novel azetidinone derivatives|

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AU601180B2|1986-04-30|1990-09-06|Kanegafuchi Kagaku Kogyo Kabushiki Kaisha|Process for preparing 4-acetoxy-3-hydroxyethylazetidin -2- one derivatives|

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CN1017991B|1987-02-20|1992-08-26|钟渊化学工业株式会社|Process for preparing 4-acetyloxy-3-hydroxyethyl azacyclo-butan-2-one derivatives|

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US5274188A|1987-05-04|1993-12-28|Ciba-Geigy Corporation|Process for the manufacture of 4-acyloxy-3-hydroxyethyl-azetidinones|

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EP0290385B1|1987-05-04|1992-10-21|Ciba-Geigy Ag|Process for preparing 4-acyloxy-3-hydroxyethyl-azetidinones|

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KR100205768B1|1996-08-24|1999-07-01|Choongwae Pharm Co|Stereo-selective composition of 4-acetoxyazetidinone|

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CN101177416B|2006-11-06|2011-06-08|上海医药工业研究院|-3-[2'--3'-hydroxy butyryl]-4-substituted oxazolidin-2-ketone derivative and preparation method thereof|

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PL227494B1|2012-12-21|2017-12-29|Inst Chemii Organicznej Polskiej Akademii Nauk|Process for preparing -4-acetoxy-3-ethyl)-2-azetidinone precursor of carbapenem antibiotics synthesis|

法律状态:

优先权:

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申请号 | 申请日 | 专利标题

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JP59139797A|JPS6118791A|1984-07-05|1984-07-05|Novel beta-lactam compound and preparation thereof|

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JP60004724A|JPH0479333B2|1985-01-14|1985-01-14|

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