【结 构 式】 |
【分子编号】45227 【品名】methyl (4aR,4bS,6aS,7S,9aS,9bS)-2-hydroxy-2,4a,6a-trimethyl-2,3,4,4a,4b,5,6,6a,7,8,9,9a,9b,10-tetradecahydroindeno[5,4-f]chromene-7-carboxylate 【CA登记号】 |
【 分 子 式 】C21H32O4 【 分 子 量 】348.48268 【元素组成】C 72.38% H 9.26% O 18.36% |
合成路线1
该中间体在本合成路线中的序号:(III)The synthesis of [14C]-labeled epristeride has been reported: The oxidation and decarboxylation of 3-oxo-4-androstene-17beta-carboxylic acid methyl ester (I) gives the 3-oxo-4-oxasteroid (II), which is methylated with [14C]-labeled methyl magnesium iodide, yielding labeled 3-hydroxy-3-methyl-4-oxa-5-androstene-17beta-carboxylic acid methyl ester (III). The cyclization of (III) by means of NaOH affords labeled 3-oxo-4-androstene-17beta-carboxylic acid methyl ester (IV), which is hydrolyzed with KOH to the corresponding acid (V). The reaction of (V) with trifluoromethanesulfonic anhydride gives the androstadiene triflate (VI), which by reaction first with SOCl2 and then with tert-butylamine is converted to the amide (VII). The carboxylation of (VII) with CO and triphenylphosphine palladium diacetate complex in methanol affords [14C]-labeled 17beta-(N-tert-butylcarbamoyl)androsta-3,5-diene-3-carboxylic acid methyl ester (VIII), which is finally treated with K2CO3 in refluxing methanol/water.
【1】 Heys, J.R.; Shu, A.Y.L.; Synthesis of carbon-14 and tritiated steroidal 5alpha-reductase inhibitors. J Label Compd Radiopharm 1994, 34, 7, 587. |
中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
---|---|---|---|---|---|---|
(I),(IV) | 14899 | methyl (8S,9S,10R,13S,14S,17S)-10,13-dimethyl-3-oxo-2,3,6,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthrene-17-carboxylate | C21H30O3 | 详情 | 详情 | |
(II) | 14924 | methyl (4aR,4bS,6aS,7S,9aS,9bS)-4a,6a-dimethyl-2-oxo-2,3,4,4a,4b,5,6,6a,7,8,9,9a,9b,10-tetradecahydroindeno[5,4-f]chromene-7-carboxylate | C20H28O4 | 详情 | 详情 | |
(III) | 14925 | methyl (4aR,4bS,6aS,7S,9aS,9bS)-2-hydroxy-2,4a,6a-trimethyl-2,3,4,4a,4b,5,6,6a,7,8,9,9a,9b,10-tetradecahydroindeno[5,4-f]chromene-7-carboxylate | C21H32O4 | 详情 | 详情 | |
(III) | 45227 | methyl (4aR,4bS,6aS,7S,9aS,9bS)-2-hydroxy-2,4a,6a-trimethyl-2,3,4,4a,4b,5,6,6a,7,8,9,9a,9b,10-tetradecahydroindeno[5,4-f]chromene-7-carboxylate | C21H32O4 | 详情 | 详情 | |
(IV) | 45228 | methyl (8S,9S,10R,13S,14S,17S)-10,13-dimethyl-3-oxo-2,3,6,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthrene-17-carboxylate | C21H30O3 | 详情 | 详情 | |
(V) | 14892 | (8S,9S,10R,13S,14S,17S)-10,13-dimethyl-3-oxo-2,3,6,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthrene-17-carboxylic acid; 4-Androstene-3-oxo-17-beta-carboxylic acid | 7385-78-6 | C20H28O3 | 详情 | 详情 |
(V) | 45229 | (8S,9S,10R,13S,14S,17S)-10,13-dimethyl-3-oxo-2,3,6,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthrene-17-carboxylic acid | C20H28O3 | 详情 | 详情 | |
(VI) | 14928 | (8S,9S,10R,13S,14S,17S)-10,13-dimethyl-3-[[(trifluoromethyl)sulfonyl]oxy]-2,7,8,9,10,11,12,13,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthrene-17-carboxylic acid | C21H27F3O5S | 详情 | 详情 | |
(VI) | 45230 | (8S,9S,10R,13S,14S,17S)-10,13-dimethyl-3-[[(trifluoromethyl)sulfonyl]oxy]-2,7,8,9,10,11,12,13,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthrene-17-carboxylic acid | C21H27F3O5S | 详情 | 详情 | |
(VII) | 14929 | (8S,9S,10R,13S,14S,17S)-17-[(tert-butylamino)carbonyl]-10,13-dimethyl-2,7,8,9,10,11,12,13,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-yl trifluoromethanesulfonate | C25H36F3NO4S | 详情 | 详情 | |
(VII) | 45231 | (8S,9S,10R,13S,14S,17S)-17-[(tert-butylamino)carbonyl]-10,13-dimethyl-2,7,8,9,10,11,12,13,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-yl trifluoromethanesulfonate | C25H36F3NO4S | 详情 | 详情 | |
(VIII) | 14930 | methyl (8S,9S,10R,13S,14S,17S)-17-[(tert-butylamino)carbonyl]-10,13-dimethyl-2,7,8,9,10,11,12,13,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthrene-3-carboxylate | C26H39NO3 | 详情 | 详情 | |
(VIII) | 45232 | methyl (8S,9S,10R,13S,14S,17S)-17-[(tert-butylamino)carbonyl]-10,13-dimethyl-2,7,8,9,10,11,12,13,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthrene-3-carboxylate | C26H39NO3 | 详情 | 详情 |