• 专利附录
  • 专利说明
  • 权利要求
  • 类似技术
  • 同族专利
  • 引用文献
  • 法律状态
  • 优先权
    • 专利摘要:
    Stereospecific synthesis of <IMAGE> (R-configuration at C2) by reaction of <IMAGE> (S-configuration at C2) with <IMAGE> at elevated temperature in the presence of a base, e.g., R-(-)-(2-(N-benzoyl-3-chloro-4-fluoroanilino)propionic acid isopropylester) from S-(-)-isopropyl lactate mesylate and 3-chloro-4-fluoroaniline followed by benzoylation. The compounds are very active herbicides against broad-leafed weeds (R=H) or wild oats (R=(thio)benzoyl).
    公开号:SU932983A3
    申请号:SU762417802
    申请日:1976-11-03
    公开日:1982-05-30
    发明作者:Марк Скотт Ричард；Дэвид Армитэйдж Джоффри
    申请人:Щелл Интернэшнл Рисерч Маатсхаппий Б.В. (Фирма)；
    IPC主号:
    专利说明:

    Example 1, Preparation. (+) 2 СЗ хпор 4 fluoroanilino) propnonic acid Slot8 methyl. mol S (-) - methi lactate mesylate and Sj-S to /; oley 3 chloro 4 "-fluoroaniline are mixed and heated for 8.5 h at 5 ° C. After cooling, the product is purified by distillation. The pure product, - (+) (3-chloro-4-fluoroanilino) -fopionic acid, methyl ester, is produced with a yield of 79% (t, kip at 0.02 mm). The rotation measured at C 2 p methanol is +79.0 grand. PRI mme R 2. Preparation of P - {-) (VI-benzoic-3-chlorop-4-fluoropa psho-propionic acid, methyl ester Mixture O, O2 mol of the product of example 1, 0.02 mol benzocl-chloride and O The molar of benzene is boiled under reflux for 2 hours. The desired product is obtained with a code of 93%; ai has a rotation value of 79 degrees. P p and m, e 3. Preparation of R - (+) (3- chloro-4-fluoroanilino) -propionic acid, isopropyl acid and a mixture of 3.0 mol 5 - {-) - isopropyl 1 lactate mesylate and 7.5 mol 3 Chlorine 4-fluoroaniline is heated at 111-14 ° C for 14 Cho 3 post-blend mixture is cooled and precipitated solid l and purified by crystallization, m.p. Zb Sv C. The yield of product was 79% rotation of 87.3 degrees. PRI me R 4. Obtaining R - {-) (N-benzoip-3-chloro-4-fluoroanilino) propionic acid, isopropyl ester. A mixture of 2.3 mol of isophopyl ether, prepared as described in Example 3, 2.4-mol of benzine chloride and 1O, O mol of toluene is boiled with a reverse holosglnik in 4 hours. The desired product, which has a melting point of 69Tl C, The yield is 96%. The magnitude of the rotation is 26.6, which indicates an estimated optical purity of 95%. PRI me R 5. Getting R - (+) - 2-3, 4-dichloroanipino) -propionic yutslot. ethyl ether. A mixture of 3.4 moles of S - (-) ethyl lactate mesylate and 8.8 moles of 3,4-dichloroaniline is heated at HO C for 24 hours. The mixture is then coagulated and given a solid product. The isolated ethyl ether is obtained with a yield of 89%, the amount of rotation is +86.0 degrees. PRI me R 6. Obtaining K () - (M-benzshl-3,4-dichloranyl) proshonic acid, ethyl ether. A mixture of 2.0 mol of ethyl ether, processed as described in the previous example, 2.1 mol of chlorogram) benzoyl and 7.7 mol of toluene was boiled under refluxing for 2 hours. The product was isolated and crystallized after crystallization. melting 86-92 ° C; Yield93%; rotation - 26.1. Example 7: Paul (now - (+) - 2 «{3, 4-dichloranyl but) -protic acid of isopropyl ether. A mixture of 2, O mol of 5 - (-) - isopropyl lactate mesylate and 5, O mol of 3,4-dichloroaniline is heated for 23 h. The mixture is cooled and a solid is isolated. After crystallization, the target ester has a tester with a pressure of B5 67 ° C. The yield is 78%, the probability is + 100.2 °. - PRI me R 8. Getting () -. 2-. - {N-benzoyl-3,4-dichloroanilino) propanoic acid, isoprohalic adjipBj. A mixture of 1.23 mol of isopropyl zf: r- "pa, obtained according to example 7 1.29 mol of benzoyl chloride and n 5 mol of toluo.yu K1; chew The melting point of the title compound, in particular, is from 51 to 53 ° C. In the increase is -31 °, the yield is 74%, Compounds SL), H, T, ZG, K, B and M are herbicidally active compounds for which the method according to the invention is automated, and compounds A, B, E F and C are intermediates for use in the preparation of herbicidally active compounds. Compounds C, HJ, and L are dextrorotatory selective herbicides against seedling weeds of P cereal crops, while compounds D, 3 t K, and M are levogram dimi selective herbicides against wild oats in cereals {% cultures. Using the procedures of Examples 1-8, A, B, E, F, Qj co-links were obtained. Physical and chemical compounds of all compounds are summarized in Table. 1. Preferred germ &amp; shchida selective against wild oats; al-cereals are shown in Table. 2. In the same place, the starting compounds and the overall yield calculated on the starting compounds.
    eleven
    权利要求:
    Claims (2)
    [1]
    Claims 1. Method for preparing general alanine derivatives of general formula 1; doow; with rnsYC -R — configuration Y and Z — hydrogen, hls or fluorine; D / is hydrogen, alkyl, C alkenyl, aryl, alkaryl, with aryshil, up to 1O atoms in lerod, aralkyl; R is hydrogen, benzoyl or thiobenzene, by reaction of a compound of the formula Tt coow -f-H CH3 in the presence of a compound of general formula when heated
    932983
    12 T a b a c a 2
    with aniline of the general formula I1 roeW, Y, Z and imeyu indicated anat-IT-O-50 -Q, where Q is alkyl or aryl containing up to 10 carbon atoms, characterized in that, in order to increase the yield of the target product and simplify the process Formulas P, where the configuration and process is carried out at 5 ° -200 C.
    [2]
    2. A method according to claim 1, characterized in that an alkali metal carbonate or bicarbonate is used as the base. Sources of information taken into account in aspergism 1. USSR Patent No. 422138, cl. С О7 С 1О1 / 44, published. 1974 (prototype).
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    同族专利:
    公开号 | 公开日
    NL7612166A|1977-05-09|
    US4267355A|1981-05-12|
    BE847891A|1977-05-03|
    DK149194B|1986-03-10|
    MX4419E|1982-04-29|
    FR2330671A1|1977-06-03|
    BR7607351A|1977-09-20|
    DE2650434C2|1989-01-26|
    IL50837D0|1977-01-31|
    CA1110268A|1981-10-06|
    DK497976A|1977-05-06|
    NL187266C|1991-08-01|
    JPS5259120A|1977-05-16|
    NL187266B|1991-03-01|
    CH623803A5|1981-06-30|
    IL50837A|1979-07-25|
    DE2650434A1|1977-05-18|
    AU507720B2|1980-02-28|
    DK149194C|1986-08-04|
    IT1063442B|1985-02-11|
    BG27539A3|1979-11-12|
    GB1563201A|1980-03-19|
    AU1927776A|1978-05-11|
    JPS6113462B2|1986-04-14|
    FR2330671B1|1979-06-08|
    引用文献:
    公开号 | 申请日 | 公开日 | 申请人 | 专利标题
    RU2481339C2|2007-11-09|2013-05-10|Аллерган, Инк.|Substituted cyclopentans possessing prostaglandin activity|GB1164160A|1966-12-30|1969-09-17|Shell Int Research|N,N-Disubstituted Amino Acid Derivatives and their use as Herbicides|
    GB1491482A|1974-02-05|1977-11-09|Shell Int Research|N,n-disubstituted alanine derivatives and their use as herbicides|DE3037159A1|1980-10-01|1982-04-15|Hoechst Ag, 6000 Frankfurt|METHOD FOR PRODUCING OPTICALLY ACTIVE 2-ANILINOPROPIONIC ACID ESTERS|
    DE3037160C2|1980-10-01|1982-09-23|Hoechst Ag, 6000 Frankfurt|Process for the preparation of optically active 2-anilinopropionic acid esters|
    JPS60109504A|1983-11-18|1985-06-15|Nissan Chem Ind Ltd|Plant growth regulating agent|
    JPH04536Y2|1984-07-04|1992-01-09|
    DE3513795A1|1985-04-17|1986-10-23|Basf Ag, 6700 Ludwigshafen|AMPHIPHILE LIQUID CRYSTAL LINKS|
    GB8521082D0|1985-08-22|1985-09-25|Ici Plc|Fungicides|
    GB8806223D0|1988-03-16|1988-04-13|Shell Int Research|Preparation of optically active n-substituted alanine herbicides|
    EP0407341B1|1989-07-05|1995-12-06|Ciba-Geigy Ag|Selective herbicidal agent|
    US5965614A|1996-11-22|1999-10-12|Athena Neurosciences, Inc.|N- amino acid esters, pharmaceutical compositions comprising same, and methods for inhibiting β-amyloid peptide release and/or its synthesis by use of such compounds|
    EP2052612A1|2007-10-24|2009-04-29|Bayer CropScience AG|Herbicide combination|
    DE102008037629A1|2008-08-14|2010-02-18|Bayer Cropscience Ag|Herbicide combination with dimethoxytriazinyl-substituted difluoromethanesulfonylanilides|
    US10172352B1|2009-12-31|2019-01-08|Lidochem, Inc.|Method for amelioration of the glyphosate effect|
    法律状态:
    优先权:
    申请号 | 申请日 | 专利标题
    GB4591475A|GB1563201A|1975-11-05|1975-11-05|Preparation of herbicidally acitve alanine derivatives|
    AU19277/76A|AU507720B2|1975-11-05|1976-11-03|Production of herbicidally active compounds|
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