　 -Drug Synthesis Database

【结构式】

【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.

参考文献中间体

合成目标

【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