Convenient Method for Synthesis of N-Protected α-Amino Epoxides: Key Intermediates for HIV Protease Inhibitors

被引：12

作者：

Blacker, A. John ^{[2
]}

Roy, Mita ^{[1
]}

Hariharan, Sivaramkrishanan ^{[1
]}

Headley, Catherine ^{[2
]}

Upare, Abhay ^{[1
]}

Jagtap, Ashutosh ^{[1
]}

Wankhede, Karuna ^{[1
]}

Mishra, Sushil Kumar ^{[1
]}

Dube, Dagadu ^{[1
]}

Bhise, Sanjay ^{[1
]}

Vishwasrao, Sandesh ^{[1
]}

Kadam, Nitin ^{[1
]}

机构：

[1] Piramal Healthcare Ltd, Bombay 400063, Maharashtra, India

[2] Piramal Healthcare UK Ltd, Huddersfield HD1 9GA, W Yorkshire, England

来源：

ORGANIC PROCESS RESEARCH & DEVELOPMENT | 2011年 / 15卷 / 02期

关键词：

BUILDING-BLOCK; EPOXIDATION;

D O I：

10.1021/op100174

中图分类号：

O69 [应用化学];

学科分类号：

081704 ;

摘要：

A convenient method for synthesis of 2R,3S and 2S,3S N-Boc phenylalanine epoxides using readily available allylamine is described. Previous methods employed multistep synthetic routes from L-phenyl alanine that include use of m-chloroperbenzoic acid (m-CPBA) and a chromatographic method for purification of the desired diastereomers. Column purification could be eliminated by bringing in much improvement in the existing process. The process was further enhanced by replacing m-CPBA with oxone, an ecofriendly reagent advantageous for commercial application. The overall green process discussed involves the recovery and recycling of enantiomers of chiral allyl amines and judicial separation of diastereomers of the epoxides using simple economical methods.

引用

页码：331 / 338

页数：8

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