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【结 构 式】 
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【分子编号】45432 【品名】(4aS,4bS,5aS,6aS,7R,8R)-7-(2-chloroacetyl)-7-hydroxy-4a,6a,8-trimethyl-5a,6,6a,7,8,9,9a,9b,10,11-decahydrocyclopenta[7,8]phenanthro[4b,5-b]oxiren-2(4aH)-one 【CA登记号】 |
【 分 子 式 】C22H27ClO4 【 分 子 量 】390.90668 【元素组成】C 67.6% H 6.96% Cl 9.07% O 16.37% |
合成路线1
该中间体在本合成路线中的序号：(III)The reaction of 9beta,11beta-epoxy-17alpha,21-dihydroxy-16alpha-methyl-1,4-pregnadiene-3,20-dione (I) with MsCl in pyridine gives the corresponding 21-mesylate (II), which is treated with LiCl in the same solvent to yield 21-chloro-9beta,11beta-epoxy-17alpha-hydroxy-16alpha-methyl-1,4-pregnadiene-3,20-dione (III). The esterification of (III) with 2-furoyl chloride (IV) and TEA affords the expected ester (IV), which is finally treated with anhydrous HCl in acetic acid in order to open the epoxide ring to provide the target mometasone furoate. A similar reaction sequence can be performed using p-toluenesulfonyl chloride instead of mesyl chloride in the first step of the sequence.
| 【1】 Shapiro, E.L. (Schering Corp.); 3,20-Dioxo-1,4-pregnanediene-17alpha-ol 17-aromatic heterocycle carboxylates. EP 0057401; US 4472393 . |
| 【2】 Tann, C.-H.; Tsai, D.J.S.; Kwok, D.-I.; Fu, X. (Schering Corp.); Process for the preparation of 17-esters of 9alpha,21-dihalo-pregnane-11beta,17alpha-diol-20-ones. WO 9800437 . |
| 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) | 45430 | (4aS,4bS,5aS,6aS,7R,8R)-7-glycoloyl-7-hydroxy-4a,6a,8-trimethyl-5a,6,6a,7,8,9,9a,9b,10,11-decahydrocyclopenta[7,8]phenanthro[4b,5-b]oxiren-2(4aH)-one | C22H28O5 | 详情 | 详情 | |
| (II) | 45431 | (4aS,4bS,5aS,6aS,7R,8R)-7-hydroxy-4a,6a,8-trimethyl-7-(2-[[methyl(dimethylene)-lambda(6)-sulfanyl]oxy]acetyl)-5a,6,6a,7,8,9,9a,9b,10,11-decahydrocyclopenta[7,8]phenanthro[4b,5-b]oxiren-2(4aH)-one | C25H34O5S | 详情 | 详情 | |
| (III) | 45432 | (4aS,4bS,5aS,6aS,7R,8R)-7-(2-chloroacetyl)-7-hydroxy-4a,6a,8-trimethyl-5a,6,6a,7,8,9,9a,9b,10,11-decahydrocyclopenta[7,8]phenanthro[4b,5-b]oxiren-2(4aH)-one | C22H27ClO4 | 详情 | 详情 | |
| (IV) | 26093 | 2-Furoyl chloride | 527-69-5 | C5H3ClO2 | 详情 | 详情 |
| (V) | 45433 | (4aS,4bS,5aS,6aS,7R,8R)-7-(2-chloroacetyl)-4a,6a,8-trimethyl-2-oxo-2,4a,5a,6,6a,7,8,9,9a,9b,10,11-dodecahydrocyclopenta[7,8]phenanthro[4b,5-b]oxiren-7-yl 2-furoate | 103213-32-7 | C27H29ClO6 | 详情 | 详情 |