Solid phase urea synthesis: An efficient and direct conversion of Fmoc-protected amines to ureas

被引：17

作者：

Chong, PY ^{[1
]}

Petillo, PA ^{[1
]}

机构：

[1] Univ Illinois, Dept Chem, Roger Adams Lab, Urbana, IL 61801 USA

来源：

TETRAHEDRON LETTERS | 1999年 / 40卷 / 24期

基金：

美国国家卫生研究院;

关键词：

D O I：

10.1016/S0040-4039(99)00820-5

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An efficient "one-pot" conversion of Fmoc-protected amino acids to the ureas in the solid phase is described. This methodology uses MeSiCl3 in the presence of Et3N to cleave Fmoc-protected amines directly to their isocyanates. This transformation has been demonstrated on some Fmoc-protected amino acids. Trapping of the resin-bound isocyanate by the addition of amines generates the desired amino acid ureas in high HPLC purities. (C) 1999 Elsevier Science Ltd. All rights reserved.

引用

页码：4501 / 4504

页数：4

共 50 条

[1] Solid phase hydantoin synthesis: An efficient and direct conversion of Fmoc-protected dipeptides to hydantoins
Chong, PY
Petillo, PA
[J]. TETRAHEDRON LETTERS, 1999, 40 (13) : 2493 - 2496
[2] ORGN 143-Direct synthesis of Fmoc-protected amines and amino acids using Fmoc-protected iminium ions
Peelen, Timothy J.
Hartman, Alison E.
Brophy, Cheryl L.
Cupp, Julia A.
Hodge, Daniel K.
Potter, Kenneth F., II
Wier, Adam D.
[J]. ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2008, 235
[3] Direct conversion of Fmoc-protected amines into O-alkyl carbamates by the Mitsunobu reaction:: a practical strategy for the solid-phase synthesis of carbamates
Zaragoza, F
Stephensen, H
[J]. TETRAHEDRON LETTERS, 2000, 41 (12) : 2015 - 2017
[4] Mild and efficient synthesis of Fmoc-protected amino azides from Fmoc-protected amino alcohols
Mondal, S
Fan, EK
[J]. SYNLETT, 2006, (02) : 306 - 308
[5] Synthesis of Fmoc-protected dicarboxyglutamic acid and its use in solid phase peptide synthesis
Nelson, JW
Capriotti, LA
Schneider, JP
[J]. ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2005, 230 : U832 - U832
[6] ORGN 637-Development of Fmoc-protected acyl imines for C-C bond-forming reactions: The direct synthesis of Fmoc-protected amines
Peelen, Timothy J.
Brophy, Cheryl L.
Hartman, Alison E.
[J]. ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2006, 232
[7] Efficient and reproducible synthesis of an Fmoc-protected Tn antigen
Piazza, Sabrina M.
Reynolds, Michael R.
Chiaramonte, Jonathan
Xu, PeiHan
Chapa-Villarreal, Fabiola A.
Trant, John F.
[J]. NEW JOURNAL OF CHEMISTRY, 2021, 45 (41) : 19224 - 19227
[8] Efficient Synthesis of Fmoc-Protected Azido Amino Acids
Lau, Yu Heng
Spring, David R.
[J]. SYNLETT, 2011, (13) : 1917 - 1919
[9] Synthesis of Fmoc-protected trans-4-methylproline
Nevalainen, M
Kauppinen, PM
Koskinen, AMP
[J]. JOURNAL OF ORGANIC CHEMISTRY, 2001, 66 (06): : 2061 - 2066
[10] Solid-phase route to Fmoc-protected cationic amino acid building blocks
Clausen, Jacob Dahlqvist
Linderoth, Lars
Nielsen, Hanne Morck
Franzyk, Henrik
[J]. AMINO ACIDS, 2012, 43 (04) : 1633 - 1641

← 1 2 3 4 5 →