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【结 构 式】

【分子编号】56622

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

【CA登记号】

【 分 子 式 】C22H29ClO3

【 分 子 量 】376.92316

【元素组成】C 70.11% H 7.75% Cl 9.41% O 12.73%

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:(XXXIII)

Condensation of 3-methoxyandrosta-3,5,9(11)-trien-17-one (XI) with (E)-1,2-dichloroethylene (XII) by means of BuLi in toluene gives 17a-[(E)-1,2-dichloro-vinyl]-17b-hydroxyandrosta-4,9(11)-dien-3-one (XXX), which is treated with phenylsulfenyl chloride and TEA in dichloromethane to yield 20,21-dichloro-21-(phenylsulfinyl)pregna-4,9(11),17(20)-trien-3-one (XXXI). Reac-tion of compound (XXXI) with MeONa in acetone/MeOH at 0 C affords 21-chloro-20-methoxy-21-(phenylsulfinyl)-pregna-4,9(11),17(20)-trien-3-one (XXXII), which by treatment with more MeONa at 35 C provides 21-chloro-17a-hydroxy-20-methoxypregna-4,9(11),20-trien-3-one (XXXIII). Hydrolysis of the enol ether of (XXXIII) with HCl in THF/acetone/MeOH gives the 3,20-dione derivative (XVI), which is finally treated with AcOK and KI in hot acetone/dichloromethane.

1 Castaner, J.; Sorbera, L.A.; Leeson, P.A.; Bayes, M.; Anecortave Acetate. Drugs Fut 2002, 27, 11, 1039.
2 Walker, J.A.; Hessler, E.J. (Pharmacia Corp.); Preparation of corticoids from 17-keto steroids. US 4357279 .
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
(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
(XII) 28793 (Z)-1,2-dichloroethene 156-59-2 C2H2Cl2 详情 详情
(XVI) 56606 (8S,10R,13S,14S,17R)-17-(2-chloroacetyl)-17-hydroxy-10,13-dimethyl-1,2,6,7,8,10,12,13,14,15,16,17-dodecahydro-3H-cyclopenta[a]phenanthren-3-one C21H27ClO3 详情 详情
(XXX) 56619 (8S,10R,13S,14S,17S)-17-[(E)-1,2-dichloroethenyl]-17-hydroxy-10,13-dimethyl-1,2,6,7,8,10,12,13,14,15,16,17-dodecahydro-3H-cyclopenta[a]phenanthren-3-one C21H26Cl2O2 详情 详情
(XXXI) 56620 (8S,10R,13S,14S)-17-[(Z)-1,2-dichloro-2-(phenylsulfinyl)ethylidene]-10,13-dimethyl-7,8,10,12,13,14,15,16-octahydro-1H-cyclopenta[a]phenanthren-3(2H,6H)-one C27H30Cl2O2S 详情 详情
(XXXII) 56621 (8S,10R,13S,14S)-17-[(Z)-2-chloro-1-methoxy-2-(phenylsulfinyl)ethylidene]-10,13-dimethyl-7,8,10,12,13,14,15,16-octahydro-1H-cyclopenta[a]phenanthren-3(2H,6H)-one C28H33ClO3S 详情 详情
(XXXIII) 56622 (8S,10R,13S,14S,17R)-17-[(E)-2-chloro-1-methoxyethenyl]-17-hydroxy-10,13-dimethyl-1,2,6,7,8,10,12,13,14,15,16,17-dodecahydro-3H-cyclopenta[a]phenanthren-3-one C22H29ClO3 详情 详情
Extended Information