申请人:Eli Lilly and Company
公开号:US04355172A1
公开(公告)日:1982-10-19
Process for 4-(D-3-amino-3-carboxypropoxy)phenylglyoxylic acid oxime as an amino-protected ester comprising alkylating an amino-protected D-methionine silyl ester with an alkyl or benzyl iodide; cyclizing the alkylsulfonium iodide to an amino-protected D-homoserine lactone; hydrolyzing the lactone to an amino-protected D-homoserine in aqueous base; coupling, to form an ether, the amino-protected D-homoserine as an ester with an ester of 4-hydroxyphenylglyoxylic acid; and forming the oxime of the ether or alternatively coupling the D-homoserine ester with a protected-oxime of an esterified 4-hydroxyphenylglyoxylic acid. The product is useful in preparing the antibiotic FR 1923.
使用4-(D-3-氨基-3-羧基丙氧基)苯甘酸肟作为氨基保护酯的过程包括:用烷基或苄基碘代物烷基化氨基保护的D-蛋氨酸硅酯;环化烷基磺鎓碘化物为氨基保护的D-高丝氨酸内酯;在水性碱中水解内酯为氨基保护的D-高丝氨酸;将氨基保护的D-高丝氨酸作为酯与4-羟基苯甘酸的酯形成醚的偶联;并形成醚的肟或者将D-高丝氨酸酯与保护肟的酯化4-羟基苯甘酸偶联。该产品在制备抗生素FR 1923中有用。