Fmoc-OASUD: A new reagent for the preparation of Fmoc-amino acids free from impurities resulting from Lossen rearrangement

被引：8
|
作者：
Rao, B. Leela Maheswara [1 ,2 ]
Nowshuddin, Shaik [1 ]
Jha, Anjali [2 ]
Divi, Murali K. [1 ]
Rao, M. N. A. [1 ]
机构：
[1] Divis Labs Ltd, Divis Res Ctr, B-34 Ind Estate, Hyderabad 500018, Andhra Pradesh, India
[2] GITAM Univ, GIS, Dept Chem, Visakhapatnam 530045, Andhra Pradesh, India
来源：
TETRAHEDRON LETTERS | 2016年 / 57卷 / 37期
关键词：
Fmoc amino acids; OH-ASUD; Fmoc-OASUD; Dipeptide; Fmoc-gabapentin; Lossen rearrangement; PROTECTING GROUPS; SUCCINIMIDYL CARBONATES; 9-FLUORENYLMETHYLOXYCARBONYL; DERIVATIVES;
D O I：
10.1016/j.tetlet.2016.08.015
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A new reagent, 9-fluorenylmethoxy-carbonyl-N-hydroxy-3-azaspiro[5,5]undecane-2,4-dione ester (Fmoc-OASUD) for the preparation of Fmoc-amino acids is described. The Fmoc-OASUD reacts with amino acids at room temperature in the presence of a base and gives Fmoc-amino acids in high yields and purity. The Fmoc-amino acids prepared using Fmoc-OASUD are free from impurities due to Lossen rearrangement, which are generally present when Fmoc-OSu is used. This is mainly because of the higher stability of Fmoc-OASUD compared to Fmoc-OSu. (C) 2016 Elsevier Ltd. All rights reserved.
引用
收藏
页码：4220 / 4223
页数：4
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