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【结 构 式】

【分子编号】56615

【品名】3-hydroxy-2-[(8S,10R,13S,14S,17R)-17-hydroxy-10,13-dimethyl-3-oxo-2,3,6,7,8,10,12,13,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-17-yl]propanenitrile

【CA登记号】

【 分 子 式 】C22H29NO3

【 分 子 量 】355.4772

【元素组成】C 74.33% H 8.22% N 3.94% O 13.5%

与该中间体有关的原料药合成路线共 1 条

合成路线1

该中间体在本合成路线中的序号:(XXVI)

Condensation of 3-methoxyandrosta-3,5,9(11)-trien-17-one (XI) with 3-hydroxypropionitrile (XXV) by means of LDA in THF provides 17a-(1-cyano-2- hydroxyethyl)-17b-hydroxyandrosta-4,9(11)-dien-3-one (XXVI), which is selectively monoacetylated by means of Ac2O in pyridine to yield monoacetate (XXVII). Dehydration of (XXVII) by means of SOCl2 in pyridine gives 20-cyano-21-acetoxypregna-4,9(11),17(20)-trien-3-one (XXVIII), which is treated with ethylene glycol, trimethyl orthoformate and TsOH in dichloromethane to afford the ethylene ketal (XXIX). Finally, compound (XXIX) is oxidized with KMnO4 in acetone/ethylene glycol and treated with NaHSO3 and HCOOH.

1 Castaner, J.; Sorbera, L.A.; Leeson, P.A.; Bayes, M.; Anecortave Acetate. Drugs Fut 2002, 27, 11, 1039.
2 Walker, J.A. (Pharmacia Corp.); Corticosteroids from 17-keto steroids via 20-cyano-DELTA17(20)-pregnanes. US 4600538 .
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
11295 Polyethylene glycol;1,2-Ethanediol;Monoethylene glycol; Ethylene glycol 107-21-1 C2H6O2 详情 详情
(XI) 18040 (8S,10R,13S,14S)-3-methoxy-10,13-dimethyl-1,2,7,8,10,12,13,14,15,16-decahydro-17H-cyclopenta[a]phenanthren-17-one C20H26O2 详情 详情
(XXV) 14029 Ethylene cyanohydrin; ECN; 3-Hydroxypropanenitrile 109-78-4 C3H5NO 详情 详情
(XXVI) 56615 3-hydroxy-2-[(8S,10R,13S,14S,17R)-17-hydroxy-10,13-dimethyl-3-oxo-2,3,6,7,8,10,12,13,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-17-yl]propanenitrile C22H29NO3 详情 详情
(XXVII) 56616 2-cyano-2-[(8S,10R,13S,14S,17R)-17-hydroxy-10,13-dimethyl-3-oxo-2,3,6,7,8,10,12,13,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-17-yl]ethyl acetate C24H31NO4 详情 详情
(XXVIII) 56617 2-cyano-2-[(8S,10R,13S,14S)-10,13-dimethyl-3-oxo-1,2,3,6,7,8,10,12,13,14,15,16-dodecahydro-17H-cyclopenta[a]phenanthren-17-ylidene]ethyl acetate C24H29NO3 详情 详情
(XXIX) 56618   C26H33NO4 详情 详情
Extended Information