申请人:MINISTERO DELL' UNIVERSITA' E DELLA RICERCA SCIENTIFICA E TECNOLOGICA
公开号:EP0351382A2
公开(公告)日:1990-01-17
New process for the synthesis of optically active aminoacids of formula
wherein R and R₁, equal or different,represent a hydrogen atom or an alkyl radical, straight or branched, containing from 1 to 6 carbon atoms, by reacting compounds of formula
wherein R and R₁ have the above seen meanings, R₂ represent a nitrile group or a COR₄ group wherein R₄ represents hydroxy or halogen or alkoxy, straight or branched,containing from 1 to 6 carbon atoms,or a OCOR₅ wherein R₅ represents an alkyl or an alkoxy group, straight or branched, containing from 1 to 6 carbon atoms and R₃ represents hydrogen, an alkyl or an alkoxy radical, straight or branched, containing from 1 to 6 carbon atoms or an aryl or aralkyl radical, with an optically active alcohol of formula
R₆-OH (III)
d or l
wherein R₆ represents an alkyl or cycloalkyl group, substituted or unsubstituted, containing from 3 to 12 carbon atoms, to obtain a pair of diastereoisomer esters of formula
which is resolved in basic medium into the single diastereoisomer esters of formula
from which the desired optically active aminoacid of formula (I) is obtained by treatment in acid medium.
式光学活性氨基酸的合成新工艺
式中 R 和 R₁,相同或不同,代表氢原子或含有 1 至 6 个碳原子的直链或支链烷基,通过与式中化合物反应,合成具有光学活性的氨基酸。
其中 R 和 R₁ 具有上述含义,R₂ 代表腈基或 COR₄ 基,其中 R₄ 代表羟基或卤素或烷氧基,直链或支链,含 1 至 6 个碳原子,或 OCOR₅,其中 R₅ 代表烷基或烷氧基、其中 R₅ 代表烷基或烷氧基,直链或支链,含 1 至 6 个碳原子,R₃ 代表氢、烷基或烷氧基,直链或支链,含 1 至 6 个碳原子,或芳基或芳烷基,与光学活性醇的化学式为
R₆-OH (III)
d 或 l
其中 R₆ 代表含有 3 至 12 个碳原子的取代或未取代的烷基或环烷基,得到一对式 R₆ 或 R₆-OH (III) 的非对映异构体酯。
在碱性介质中分解成单非对映异构体的式
在酸性介质中进行处理,从中得到所需光学活性的式 (I) 氨基酸。