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【结 构 式】

【分子编号】21670

【品名】tert-butyl (2S)-2-[(1R)-1-([[(1S)-1-benzyl-2-oxo-2-phenylethyl]amino]carbonyl)-3-methylbutyl]-4-pentenoate

【CA登记号】

【 分 子 式 】C30H39NO4

【 分 子 量 】477.644

【元素组成】C 75.44% H 8.23% N 2.93% O 13.4%

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:(V)

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

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) 12874 (2R)-2-[(tert-Butoxycarbonyl)amino]-3-phenylpropionic acid; N-alpha-t-BOC-L-Phenylalanine 13734-34-4 C14H19NO4 详情 详情
(II) 21667 tert-butyl (1S)-1-benzyl-2-oxo-2-phenylethylcarbamate 202861-97-0 C20H23NO3 详情 详情
(III) 21668 (2S)-2-amino-1,3-diphenyl-1-propanone hydrochloride C15H16ClNO 详情 详情
(IV) 21641 1-(tert-butyl) 4-(2,3,4,5,6-pentafluorophenyl) (2S,3R)-2-allyl-3-isobutylbutanedioate C21H25F5O4 详情 详情
(V) 21670 tert-butyl (2S)-2-[(1R)-1-([[(1S)-1-benzyl-2-oxo-2-phenylethyl]amino]carbonyl)-3-methylbutyl]-4-pentenoate C30H39NO4 详情 详情
(VI) 21671 (2S)-2-[(1R)-1-([[(1S)-1-benzyl-2-oxo-2-phenylethyl]amino]carbonyl)-3-methylbutyl]-4-pentenoic acid C26H31NO4 详情 详情
(VII) 21644 (Aminooxy)(tert-butyl)dimethylsilane; O-[tert-Butyl(dimethyl)silyl]hydroxylamine 41879-39-4 C6H17NOSi 详情 详情
Extended Information