methyl (2R)-2-(acetamido)-3-[4-(acetamido)-3-chlorophenyl]propanoate -Drug Synthesis Database

【结构式】

【分子编号】34371

【品名】methyl (2R)-2-(acetamido)-3-[4-(acetamido)-3-chlorophenyl]propanoate

【CA登记号】

【分子式】C₁₄H₁₇ClN₂O₄

【分子量】312.75276

【元素组成】C 53.77% H 5.48% Cl 11.34% N 8.96% O 20.46%

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：(IV)

The intermediate 3-chloro-4-amino-D-phenylalanine (V) was synthesized from 4-amino-D-phenylalanine (I). Esterification with a methanolic solution of HCl, prepared from MeOH and AcCl, gave methyl ester (II), and subsequent acylation by means of Ac2O and pyridine afforded diacetamide (III). Halogenation of (III) using N-chlorosuccinimide produced chloride (IV). Basic hydrolysis of (IV) cleaved the methyl ester and one of the acetyl groups, and subsequent treatment with strong acid removed the remaining acetyl group yielding (V).

参考文献中间体

合成目标

【1】 Schultz, R.M.; Andis, S.L.; Ray, J. E.; Patel, V.F.; Kennedy, J.H.; Novel cryptophycin antitumor agents: Synthesis and cytotoxicity of fragment "B" analogues. J Med Chem 1999, 42, 14, 2588.

中间体序号	中间体编号	品名	分子式	供应商	用于合成
(I)	34368	(2R)-2-amino-3-(4-aminophenyl)propionic acid	C₉H₁₂N₂O₂	详情	详情
(II)	34369	methyl (2R)-2-amino-3-(4-aminophenyl)propanoate	C₁₀H₁₄N₂O₂	详情	详情
(III)	34370	methyl (2R)-2-(acetamido)-3-[4-(acetamido)phenyl]propanoate	C₁₄H₁₈N₂O₄	详情	详情
(IV)	34371	methyl (2R)-2-(acetamido)-3-[4-(acetamido)-3-chlorophenyl]propanoate	C₁₄H₁₇ClN₂O₄	详情	详情
(V)	34372	(2R)-2-amino-3-(4-amino-3-chlorophenyl)propionic acid	C₉H₁₁ClN₂O₂	详情	详情

Extended Information