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    Process for the synthesis of chirally pure beta-amino-alcohols
    8.
    发明授权
    Process for the synthesis of chirally pure beta-amino-alcohols 失效
    手性纯合β-氨基醇的合成方法

    公开(公告)号：US06800764B2

    公开(公告)日：2004-10-05

    申请号：US10304322

    申请日：2002-11-26

    申请人： Anthony Frank Kreft ,  Madelene Miyoko Antane ,  Derek Cecil Cole ,  Dennis Martin Kubrak ,  Lynn Resnick ,  Joseph Raymond Stock ,  Zheng Wang

    发明人： Anthony Frank Kreft ,  Madelene Miyoko Antane ,  Derek Cecil Cole ,  Dennis Martin Kubrak ,  Lynn Resnick ,  Joseph Raymond Stock ,  Zheng Wang

    IPC分类号： C07D33332

    CPC分类号： C07C215/20 ,  C07B2200/07 ,  C07C215/08 ,  C07C215/24 ,  C07C215/28 ,  C07C215/56 ,  C07C229/08 ,  C07C229/28 ,  C07C229/30 ,  C07C229/36 ,  C07C247/12 ,  C07C323/63 ,  C07D263/26 ,  C07D333/34

    摘要： A process is provided for preparing chirally pure S-enantiomers of &agr;-amino acids comprising the steps of: a) preparing an organometallic reagent from an alkyl halide of the formula (R)2CH(CH2)nCH2X; b) adding the organometallic reagent to carbon dioxide to afford a carboxylic acid; c) activating the carboxylic acid with an acid chloride, phosphorus trichloride, acid anhydride, or thionyl chloride in the presence of a tertiary amine base; d) reacting the product of step c) with an alkali metal salt of S-4-benzyl-2-oxazolidinone; e) treating the product of step d) with a strong non-nucleophilic base to form an enolate anion; f) trapping the enolate anion with 2,4,6-triisopropylbenzenesulfonyl azide to afford an oxazolidinone azide; g) hydrolyzing the oxazolidinone azide with an aqueous base to afford an &agr;-azido acid; h) reducing the &agr;-azido acid to the &agr;-amino acid; and i) recrystallizing the &agr;-amino acid to the chirally pure &agr;-amino acid. A process is also provided for preparing chirally pure S-enantiomers of &bgr;-amino alcohols further comprising the steps of reducing the crude &agr;-amino acid to the &bgr;-amino alcohol and recrystallizing the &bgr;-amino alcohol to the chirally pure &bgr;-amino alcohol. A process is further provided for preparing chirally pure S enantiomers of N-sulfonyl &bgr;-amino alcohols further comprising the steps of sulfonylating the &bgr;-amino alcohol with 5-chloro-thiophene-2-sulfonyl halide; and recrystallizing to afford the chirally pure N-sulfonyl &bgr;-amino alcohols.

    摘要翻译： 提供了一种用于制备α-氨基酸的手性纯的S-对映异构体的方法，包括以下步骤：a）由式（R）2CH（CH 2）n CH 2 X的烷基卤制备有机金属试剂; b）将有机金属试剂加入到二氧化碳中，得到羧酸; c）在叔胺碱存在下用酰氯，三氯化磷，酸酐或亚硫酰氯活化羧酸; d）使步骤c）的产物与S-4-苄基-2-恶唑烷酮的碱金属盐反应; e）用强非亲核碱处理步骤d）的产物以形成烯醇化物阴离子; f）用2,4,6-三异丙基苯磺酰叠氮化物捕获烯醇化阴离子，得到恶唑烷酮叠氮化物; g）用碱水溶液水解恶唑烷酮叠氮化物，得​​到α-叠氮基; h）将α-叠氮基还原成α-氨基酸; 和i）将α-氨基酸重结晶至手性纯的α-氨基酸。 还提供了制备β-氨基醇的手性纯的S-对映异构体的方法，该方法还包括将β-氨基酸的粗α-氨基酸还原成β-氨基醇，并将β-氨基醇重结晶至手性纯的β-氨基醇 。 还提供了制备N-磺酰基β-氨基醇的手性纯S对映异构体的方法，其还包括用5-氯 - 噻吩-2-磺酰卤磺酰化β-氨基醇的步骤; 并重结晶得到手性纯的N-磺酰基β-氨基醇。