tert-butyl 1-benzyl-2-oxo-2-(2-thienyl)ethylcarbamate -Drug Synthesis Database

【结构式】

【分子编号】21683

【品名】tert-butyl 1-benzyl-2-oxo-2-(2-thienyl)ethylcarbamate

【CA登记号】

【分子式】C₁₈H₂₁NO₃S

【分子量】331.43568

【元素组成】C 65.23% H 6.39% N 4.23% O 14.48% S 9.67%

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)

Condensation of N-(tert-butoxycarbonyl)phenylalanine methyl ester (I) with 2-thienyllithium (II) in THF at -78 C furnished racemized ketone (III). The N-Boc group of (III) was deprotected with HCl in dioxan to yield aminoketone (IV), which was then condensed with the succinate building block (V) in DMF to afford succinamide (VI). Further deprotection of the tert-butyl ester of (VI) by treatment with trifluoroacetic acid provided carboxylic acid (VII), which was coupled with O-tert-butyldimethylsilyl hydroxylamine (VIII) in the presence of EDC and HOBt to yield, after desilylation, the target hydroxamic acid.

参考文献中间体

合成目标

【1】 Sheppard, G.S.; Florjancic, A.S.; Giesler, J.R.; Xu, L.; Guo, Y.; Davidsen, S.K.; Marcotte, P.A.; Elmore, I.; Albert, D.H.; Terrance, J.M.; Bouska, J.J.; Goodfellow, C.L.; Morgan, D.W.; Summers, J.B.; Aryl ketones as novel replacements for the C-terminal amide bond of succinyl hydroxamate MMP inhibitors. Bioorg Med Chem Lett 1998, 8, 22, 3251.

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)	21673	methyl (2S)-2-[(tert-butoxycarbonyl)amino]-3-phenylpropanoate		C₁₅H₂₁NO₄	详情	详情
(II)	21682	2-thienyllithium	2786-07-4	C₄H₃LiS	详情	详情
(III)	21683	tert-butyl 1-benzyl-2-oxo-2-(2-thienyl)ethylcarbamate		C₁₈H₂₁NO₃S	详情	详情
(IV)	21684	2-amino-3-phenyl-1-(2-thienyl)-1-propanone hydrochloride		C₁₃H₁₄ClNOS	详情	详情
(V)	21641	1-(tert-butyl) 4-(2,3,4,5,6-pentafluorophenyl) (2S,3R)-2-allyl-3-isobutylbutanedioate		C₂₁H₂₅F₅O₄	详情	详情
(VI)	21686	tert-butyl (2S)-2-[(1R)-1-([[1-benzyl-2-oxo-2-(2-thienyl)ethyl]amino]carbonyl)-3-methylbutyl]-4-pentenoate		C₂₈H₃₇NO₄S	详情	详情
(VII)	21687	(2S)-2-[(1R)-1-([[1-benzyl-2-oxo-2-(2-thienyl)ethyl]amino]carbonyl)-3-methylbutyl]-4-pentenoic acid		C₂₄H₂₉NO₄S	详情	详情
(VIII)	21644	(Aminooxy)(tert-butyl)dimethylsilane; O-[tert-Butyl(dimethyl)silyl]hydroxylamine	41879-39-4	C₆H₁₇NOSi	详情	详情

Extended Information