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【结 构 式】 
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【分子编号】54929 【品名】 【CA登记号】 |
【 分 子 式 】C27H35F2NO6S 【 分 子 量 】539.6408464 【元素组成】C 60.09% H 6.54% F 7.04% N 2.6% O 17.79% S 5.94% |
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：(VI)The oxidation of flumethasone (I) with Pd(OAc)2, PPh3 and IO4H in DMA gives the 17-beta-carboxylic acid (II), which is selectively monoacylated with propionyl chloride (III) and Et2NH in acetone, yielding the 17-alpha-propionyloxy derivative (IV). The reaction of (IV) with N,N-dimethylthiocarbamoyl chloride (V), TEA and NaI in 2-butanone affords the thioanhydride (VI), which is finally treated with chlorofluoromethane and SHNa in DMA to provide the desired fluoromethyl thioester.
| 【1】 Cooper, A.J.; Chamberlin, S.A.; Hufnagel, J.J.; Barkalow, J.; Hossain, A.; Langridge, D.C. (Abbott Laboratories Inc.); Method for the preparation of fluticasone and related 17betaETA-carbothioic esters using a novel carbothioic acid synthesis and novel purification methods. WO 0162722 . |
| 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) | 14475 | (6S,8S,9R,10S,11S,13S,14S,16R,17R)-6,9-difluoro-17-glycoloyl-11,17-dihydroxy-10,13,16-trimethyl-6,7,8,9,10,11,12,13,14,15,16,17-dodecahydro-3H-cyclopenta[a]phenanthren-3-one | 2557-49-5 | C22H28F2O5 | 详情 | 详情 |
| (II) | 14476 | (6S,8S,9R,10S,11S,13S,14S,16R,17R)-6,9-difluoro-11,17-dihydroxy-10,13,16-trimethyl-3-oxo-6,7,8,9,10,11,12,13,14,15,16,17-dodecahydro-3H-cyclopenta[a]phenanthrene-17-carboxylic acid | C21H26F2O5 | 详情 | 详情 | |
| (III) | 15967 | propanoyl chloride; propionyl chloride | 79-03-8 | C3H5ClO | 详情 | 详情 |
| (IV) | 14477 | (6S,8S,9R,10S,11S,13S,14S,16R,17R)-6,9-difluoro-11-hydroxy-10,13,16-trimethyl-3-oxo-17-(propionyloxy)-6,7,8,9,10,11,12,13,14,15,16,17-dodecahydro-3H-cyclopenta[a]phenanthrene-17-carboxylic acid | C24H30F2O6 | 详情 | 详情 | |
| (V) | 54928 | Dimethylthiocarbamoyl chloride; N,N-Dimethylthiocarbamoyl chloride | 16420-13-6 | C3H6ClNS | 详情 | 详情 |
| (VI) | 54929 | C27H35F2NO6S | 详情 | 详情 | ||
| (VII) | 54930 | Chlorofluoromethane; Monochloromonofluoromethane | 593-70-4 | CH2ClF | 详情 | 详情 |
Extended Information