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    • 5. 发明申请
    • Process for Preparing Enantiopure E-(2S)-Alkyl-5-Halopent-4-Enoic Acids and Esters
    • 制备对映体(E)(2S) - 烷基-5-卤代-4-烯酸和酯的方法
    • US20080281125A1
    • 2008-11-13
    • US11885740
    • 2006-02-22
    • Markus RosslerGerhard SteinbauerPeter Pojarliev
    • Markus RosslerGerhard SteinbauerPeter Pojarliev
    • C07C51/42
    • C07C51/02C07B2200/07C07C51/412C07C51/43C07C57/52
    • A process for preparing enantiopure E-(2S)-alkyl-5-halopent-4-enoic acids and their esters of the formula (I), in which R is a C1-C6-alkyl radical, R1 is H or C1-C4-alkyl and X is chlorine, bromine or iodine, in which the corresponding racemic 2-alkyl-5-halopent-4-enoic acid a) is reacted in a suitable solvent first with (S)-3-Methyl-2-phenylbutylamine, quinine or with N-methyl-D-glucamine, after which b) the corresponding (S)-3-Methyl-2-phenylbutylamine salt, quinine or glucamine salt of the (R)-pentenoic acid is precipitated and removed, and c) the remaining filtrate is mixed with a second chiral base or an inorganic salt, after which the corresponding salt of the (S)-pentenoic acid is precipitated and d) is then converted into the corresponding E-(2S)-alkyl-5-halo-4-pentenoic acid and subsequently where appropriate into the corresponding ester of the formula (I) in which R1 is C1-C4-alkyl.
    • 一种制备对映体育用的E-(2S) - 烷基-5-卤代-4-烯酸及其式(I)的酯的方法,其中R是C 1 -C 6 - 6个 - 烷基,R 1是H或C 1 -C 4 - 烷基,X是氯,溴或碘 其中相应的外消旋的2-烷基-5-卤代-4-烯酸a)在合适的溶剂中首先与(S)-3-甲基-2-苯基丁胺,奎宁或与N-甲基-D-葡萄糖胺 ,然后b)相应的(S)-3-甲基-2-苯基丁胺盐,(R) - 戊烯酸的奎宁或葡糖胺盐沉淀并除去,和c)将剩余的滤液与第二手性碱 或无机盐,然后将(S) - 戊烯酸的相应盐沉淀出来,然后将d)转化成相应的E-(2S) - 烷基-5-卤代-4-戊烯酸,随后适当地加入 其中R 1为C 1 -C 4 - 烷基的式(I)的相应酯。
    • 10. 发明授权
    • Process for preparing racemic alkyl-5-halopent-4-enecarboxylic acids or carboxylic esters
    • 制备外消旋烷基-5-卤代-4-烯羧酸或羧酸酯的方法
    • US07550626B2
    • 2009-06-23
    • US11995553
    • 2006-07-03
    • Peter PojarlievGerhard SteinbauerChristian Burger
    • Peter PojarlievGerhard SteinbauerChristian Burger
    • C07C69/62C07C53/15
    • C07C51/09C07C67/32C07C67/343C07C57/52C07C69/65
    • A process for preparing racemic alkyl-5-halopent-4-enecarboxylic acids and esters thereof of the formula (I), in which R is a C1-C6-alkyl radical, R1 is H or C1-4-alkyl and X is chlorine, bromine or iodine, which comprises a) reacting a dialkyl alkylmalonate of the formula (II),in which R is as defined above and R2 is a C1-C4-alkyl radical, in the presence of a metal alkoxide of the formula MOR3, in which M may be Na, K or Li, and R3 is a C1-C4-alkyl radical, and in an organic solvent, with 1,3-dihalopropene to give the corresponding allylated malonate, then b) after full conversion, adding an inorganic salt and a C1-C6 alcohol to the reaction mixture, heating the reaction mixture to reflux temperature, then c) isolating the desired racemic ester of the formula (I) from the reaction mixture by extraction or direct distillation and d) if the racemic acid is the desired end product, hydrolyzing the ester function.
    • 制备式(I)的外消旋烷基-5-卤代-4-甲酸及其酯的方法,其中R是C1-C6-烷基,R1是H或C1-4 - 烷基,X是氯 溴或碘,其包括:a)在式MOR 3的金属醇盐存在下使式(II)的烷基丙二酸二烷基酯(其中R如上定义,R 2是C 1 -C 4 - 烷基) 其中M可以是Na,K或Li,R3是C1-C4-烷基,在有机溶剂中与1,3-二卤丙烯反应,得到相应的烯丙基化丙二酸酯,然后b)完全转化后,加入 无机盐和C 1 -C 6醇反应混合物,将反应混合物加热至回流温度,然后c)通过萃取或直接蒸馏从反应混合物中分离所需的式(I)外消旋酯,和d)如果外消旋 酸是所需的最终产物,水解酯的功能。