methyl (2R)-2-amino-3-[(4-phenoxyphenyl)sulfonyl]propanoate -Drug Synthesis Database

【结构式】

【分子编号】51658

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

【CA登记号】

【分子式】C₁₆H₁₇NO₅S

【分子量】335.38072

【元素组成】C 57.3% H 5.11% N 4.18% O 23.85% S 9.56%

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 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.

参考文献中间体

合成目标

【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	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