Vincamine → (+)-Apovincaminic acid

HRID 1632287

반응식

HRID 1632287 반응식
[CH3:1][CH2:2][C@:3]12[CH2:19][C@:18](O)([C:20]([O:22]C)=[O:21])[N:17]3[C:9]4=[C:10]([CH2:25][CH2:26][N:7]([C@@H:8]14)[CH2:6][CH2:5][CH2:4]2)[C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][C:16]=13.CC[C@]12C=C(C(OC)=O)N3C4=C(CCN([C@@H]14)CCC2)C1C=CC=CC=13>O>[CH3:1][CH2:2][C@:3]12[CH:19]=[C:18]([C:20]([OH:22])=[O:21])[N:17]3[C:9]4=[C:10]([C:11]5[C:16]3=[CH:15][CH:14]=[CH:13][CH:12]=5)[CH2:25][CH2:26][N:7]([C@@H:8]14)[CH2:6][CH2:5][CH2:4]2

참가 물질

4

반응물 2

HCID 15376VincamineHCID 71204Apovincamine

생성물 1

HCID 160154(+)-Apovincaminic acid수율 60%

시약·촉매·용매 1

HCID 962Water용매2회

실험 절차

According to the Hungarian Patent Specification No. 163,143 racemic, cis compounds of the formula (I) and optically active, cis compound of the formula (Ic) were prepared by hydrolyzing the pharmaceutically active vincamine and converting the vincaminic acid obtained into a desired ester from which the corresponding apovincaminic acid ester was obtained by splitting off water; or alternatively, vincamine was first converted into apovincamine by splitting off water which was then subjected to hydrolysis and the apovincaminic acid obtained was converted into a desired ester. This process is disadvantageous in that at first vincamine should be prepared by a multi-step synthesis from which the corresponding apovincaminic acid esters can be prepared with a yield of at most 60% only.

후처리

  1. customwas then subjected to hydrolysis

출처 및 근거

ORD 기록
ord-44d6c4a287d4486689885cbf94ee5dfd
출처 데이터셋
uspto-grants-1984_10
특허 번호
US04474960

연결된 노트

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