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【结 构 式】

【分子编号】51659

【品名】methyl (2R)-2-(methylamino)-3-[(4-phenoxyphenyl)sulfonyl]propanoate

【CA登记号】

【 分 子 式 】C17H19NO5S

【 分 子 量 】349.4076

【元素组成】C 58.44% H 5.48% N 4.01% O 22.9% S 9.18%

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:(VII)

The reaction of N-(benzyloxycarbonyl)-L-serine methyl ester (I) with Ts-Cl gives the corresponding tosylate (II), which is condensed with 4-phenoxythiophenol (III) to yield the thioether (IV). The oxidation of (IV) with Oxone affords the sulfone (V), which is N-deprotected with H2 over Pd/C to provide compound (VI) with a free amino group. The methylation of (VI) with methyl iodide gives the N-methyl derivative (VII), which is finally treated with hydroxylamine to afford the target hydroxamic acid.

1 Bedell, L.; Becker, D.P.; Barta, T.E.; et al.; alpha-Amino-beta-sulphone hydroxamates as potent MMP-13 inhibitors that spare MMP-1. Bioorg Med Chem Lett 2001, 11, 20, 2719.
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) 51660 methyl (2S)-2-[[(benzyloxy)carbonyl]amino]-3-hydroxypropanoate C12H15NO5 详情 详情
(II) 51655 methyl (2S)-2-[[(benzyloxy)carbonyl]amino]-3-[[(4-methylphenyl)sulfonyl]oxy]propanoate C19H21NO7S 详情 详情
(III) 26254 4-phenoxybenzenethiol; 4-phenoxyphenylhydrosulfide C12H10OS 详情 详情
(IV) 51656 methyl (2R)-2-[[(benzyloxy)carbonyl]amino]-3-[(4-phenoxyphenyl)sulfanyl]propanoate C24H23NO5S 详情 详情
(V) 51657 methyl (2R)-2-[[(benzyloxy)carbonyl]amino]-3-[(4-phenoxyphenyl)sulfonyl]propanoate C24H23NO7S 详情 详情
(VI) 51658 methyl (2R)-2-amino-3-[(4-phenoxyphenyl)sulfonyl]propanoate C16H17NO5S 详情 详情
(VII) 51659 methyl (2R)-2-(methylamino)-3-[(4-phenoxyphenyl)sulfonyl]propanoate C17H19NO5S 详情 详情
Extended Information