9H-fluoren-9-ylmethyl (3R,6S,8aS)-3-[(Z)-7-[(tert-butoxycarbonyl)amino]-11,11-dimethyl-9-oxo-10-oxa-2,6,8-triaza-7-dodecen-1-anoyl]-5-oxohexahydro-5H-[1,3]thiazolo[3,2-a]pyridin-6-ylcarbamate -Drug Synthesis Database

【结构式】

【分子编号】26833

【品名】9H-fluoren-9-ylmethyl (3R,6S,8aS)-3-[(Z)-7-[(tert-butoxycarbonyl)amino]-11,11-dimethyl-9-oxo-10-oxa-2,6,8-triaza-7-dodecen-1-anoyl]-5-oxohexahydro-5H-[1,3]thiazolo[3,2-a]pyridin-6-ylcarbamate

【CA登记号】

【分子式】C₃₇H₄₈N₆O₈S

【分子量】736.88976

【元素组成】C 60.31% H 6.57% N 11.4% O 17.37% S 4.35%

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：(III)

Coupling of thiazolopyridine (I) with amine (II) in the presence of EDC and HOBt provided amide (III). Deprotection of the Fmoc group of (III) was effected with piperidine in CH2Cl2 and the resulting amine (IV) was condensed with benzylsulfonyl chloride (V) to afford sulfonamide (VI). Finally, both Boc protecting groups of (VI) were removed with TFA to yield the title guanidine as the bis(trifluoroacetate) salt.

参考文献中间体

合成目标

【1】 Wagner, J.; Kallen, J.; Ehrhardt, C.; Evenou, J.-P.; Wagner, D.; Rational design, synthesis, and X-ray structure of selective noncovalent thrombin inhibitors. J Med Chem 1998, 41, 19, 3664.

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)	26832	(3R,6S,8aS)-6-[[(9H-fluoren-9-ylmethoxy)carbonyl]amino]-5-oxohexahydro-5H-[1,3]thiazolo[3,2-a]pyridine-3-carboxylic acid		C₂₃H₂₂N₂O₅S	详情	详情
(II)	26836	tert-butyl (Z)-[(3-aminopropyl)amino][(tert-butoxycarbonyl)amino]methylidenecarbamate		C₁₄H₂₈N₄O₄	详情	详情
(III)	26833	9H-fluoren-9-ylmethyl (3R,6S,8aS)-3-[(Z)-7-[(tert-butoxycarbonyl)amino]-11,11-dimethyl-9-oxo-10-oxa-2,6,8-triaza-7-dodecen-1-anoyl]-5-oxohexahydro-5H-[1,3]thiazolo[3,2-a]pyridin-6-ylcarbamate		C₃₇H₄₈N₆O₈S	详情	详情
(IV)	26834	tert-butyl (Z)-[[3-([[(3R,6S,8aS)-6-amino-5-oxohexahydro-5H-[1,3]thiazolo[3,2-a]pyridin-3-yl]carbonyl]amino)propyl]amino][(tert-butoxycarbonyl)amino]methylidenecarbamate		C₂₂H₃₈N₆O₆S	详情	详情
(V)	25151	phenylmethanesulfonyl chloride	1939-99-7	C₇H₇ClO₂S	详情	详情
(VI)	26835	tert-butyl (Z)-([3-[([(3R,6S,8aS)-6-[(benzylsulfonyl)amino]-5-oxohexahydro-5H-[1,3]thiazolo[3,2-a]pyridin-3-yl]carbonyl)amino]propyl]amino)[(tert-butoxycarbonyl)amino]methylidenecarbamate		C₂₉H₄₄N₆O₈S₂	详情	详情

Extended Information