Activation of carboxylic acids as their active esters by means of tert-butyl 3-(3,4-dihydrobenzotriazine-4-on)yl carbonate

被引：25

作者：

Basel, Y ^{[1
]}

Hassner, A ^{[1
]}

机构：

[1] Bar Ilan Univ, Dept Chem, IL-52900 Ramat Gan, Israel

来源：

TETRAHEDRON LETTERS | 2002年 / 43卷 / 14期

关键词：

D O I：

10.1016/S0040-4039(02)00324-6

中图分类号：

O62 [有机化学];

学科分类号：

070303 [有机化学]; 081704 [应用化学];

摘要：

Carboxylic acids were activated in the presence of DMAP with tert-butyl carbonates (BOC-OX) 1, which were prepared in situ by reaction of X-OH and di-tert-butyl dicarbonate (BOC2O). The most efficient active carbonate proved to be tert-butyl 3-(3,4-dihydrobenzotriazine-4-on)yl carbonate la, leading to efficient formation of benzotriazinonyl esters 3 and 6, which are intermediates in reactions with primary and secondary amines to afford amides or peptides in good yield. By-products in the formation of 3 or 6 are the environmentally safe tert-BuOH and CO2. The hindered amino acid AIB also forms a dipeptide in good yield. (C) 2002 Elsevier Science Ltd. All rights reserved.

引用

页码：2529 / 2533

页数：5

共 14 条

[1]

PEPTIDE-SYNTHESIS .12. 3,4-DIHYDRO-4-OXO-1,2,3-BENZOTRIAZIN-3-YL ESTERS OF FLUORENYLMETHOXYCARBONYL AMINO-ACIDS AS SELF-INDICATING REAGENTS FOR SOLID-PHASE PEPTIDE-SYNTHESIS [J].