Simple and Mild One-Pot Synthesis of Dipeptidyl Ureas via Carbamoyl Azides of -N-Protected Amino Acids

被引：1

作者：

Venneri, Cesare Daniele ^{[1
]}

Verardo, Giancarlo ^{[1
]}

Strazzolini, Paolo ^{[1
]}

机构：

[1] Univ Udine, Dept Chem Sci & Technol, I-33100 Udine, Italy

来源：

SYNTHETIC COMMUNICATIONS | 2011年 / 41卷 / 07期

关键词：

Amino acid methyl esters; amino acids; carbamoyl azide; Curtius rearrangement; dipeptidyl ureas; SOLID-PHASE SYNTHESIS; HIV-1 PROTEASE INHIBITORS; ARTIFICIAL BETA-SHEETS; PEPTIDYL UREAS; EFFICIENT SYNTHESIS; GAMMA-SECRETASE; UNNATURAL BIOPOLYMERS; DRUG DISCOVERY; ACTIVE-SITE; DERIVATIVES;

D O I：

10.1080/00397911003710570

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

[image omitted] A simple and mild one-pot synthesis of potentially bioactive -N-protected dipeptidyl ureas is reported. The procedure involves the reaction between the carbamoyl azide of an -N-protected amino acid and an -amino acid methyl ester. The reaction is fast (3h at 45 degrees C), regardless of the nature of both the reagents, and racemization free. The reported protocol represents a valid alternative to existing methods.

引用

页码：1027 / 1041

页数：15

共 50 条

[1] Carbamoyl azides of α-N-protected amino acids:: A fast and simple one-pot synthesis
Verardo, Giancarlo
Bombardella, Elisa
Geatti, Paola
Strazzolini, Paolo
SYNTHESIS-STUTTGART, 2008, (03): : 438 - 444
[2] A Convenient Synthesis of Unsymmetrically Substituted Ureas via Carbamoyl Azides of α-N-Protected Amino Acids
Verardo, Giancarlo
Bombardella, Elisa
Venneri, Cesare Daniele
Strazzolini, Paolo
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2009, 2009 (35) : 6239 - 6244
[3] 'ONE-POT' PREPARATION OF N-PROTECTED AMINO ACIDS VIA THE AZIDE METHOD
Cruz, L. J.
Beteta, N. G.
Ewenson, A.
Albericio, F.
JOURNAL OF PEPTIDE SCIENCE, 2004, 10 : 145 - 145
[4] One-Pot Conversion of Benzyl Alcohols to N-Protected Anilines and Alkyl Alcohols to Carbamoyl Azides
Kobayashi, Shoji
Yamaguchi, Ryo
Yamamoto, Fumiya
Komori, Jun
Sakamoto, Hotaka
Kasashima, Takahiro
Adriaenssens, Louis
Lear, Martin J.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2023, 26 (47)
[5] One-pot synthesis of N-protected β-chiral amino alcohols
Somlai, C
Péter, A
Forgó, P
Penke, B
SYNTHETIC COMMUNICATIONS, 2003, 33 (11) : 1815 - 1820
[6] One-pot synthesis of enantiomerically pure N-protected allylic amines from N-protected α-amino esters
Silveira-Dorta, Gaston
Alvarez-Mendez, Sergio J.
Martin, Victor S.
Padron, Jose M.
BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY, 2016, 12 : 957 - 962
[7] Study of the Reaction between Carbamoyl Azides of α-N-Protected Amino Acids and Hydrazine Monohydrate
Verardo, Giancarlo
Venneri, Cesare Daniele
Esposito, Gennaro
Strazzolini, Paolo
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2011, 2011 (07) : 1376 - 1384
[8] CONVENIENT ONE-POT ESTERIFICATION OF N-PROTECTED AMINO-ACIDS VIA ISOPROPENYL CHLOROFORMATE ACTIVATION
JOUIN, P
CASTRO, B
ZEGGAF, C
PANTALONI, A
SENET, JP
LECOLIER, S
SENNYEY, G
TETRAHEDRON LETTERS, 1987, 28 (15) : 1661 - 1664
[9] A CONVENIENT ONE-POT CONVERSION OF N-PROTECTED AMINO-ACIDS AND PEPTIDES INTO ALCOHOLS
KOKOTOS, G
SYNTHESIS-STUTTGART, 1990, (04): : 299 - 301
[10] SYNTHESIS OF N-PROTECTED OMEGA-AMINO ACIDS WITH AID OF STANNYL AZIDES
KRICHELDORF, HR
SCHWARZ, G
KASCHIG, J
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1977, 16 (08): : 550 - 552

← 1 2 3 4 5 →