Vincamine → (+)-Apovincaminic acid

HRID 1632287

反応式

HRID 1632287 の反応式
[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

参加物

4

反応物 2

HCID 15376VincamineHCID 71204Apovincamine

生成物 1

HCID 160154(+)-Apovincaminic acid収率 60%

試薬・触媒・溶媒 1

HCID 962Water溶媒2 回

実験手順

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.

後処理

  1. customwas then subjected to hydrolysis

出典と根拠

ORDレコード
ord-44d6c4a287d4486689885cbf94ee5dfd
出典データセット
uspto-grants-1984_10
特許番号
US04474960

関連ノート

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