One-pot process to Z-α-benzoylamino-acrylic acid methyl esters via potassium phosphate-catalyzed Erlenmeyer reaction

被引:27
作者
Cleary, Thomas [1 ]
Brice, Jodie [1 ]
Kennedy, Nicole [1 ]
Chavez, Flavio [1 ]
机构
[1] Roche Carolina Inc, PTDA FL, Florence, SC 29506 USA
关键词
Erlenmeyer reaction; Acrylic acids; Oxazolones; UNUSUAL AMINO-ACIDS; ASYMMETRIC HYDROGENATION; DERIVATIVES; ISOMERS;
D O I
10.1016/j.tetlet.2009.11.081
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A practical and efficient two reaction sequence one-pot process for the synthesis of Z-alpha-benzoylaminoacrylic acid methyl esters was developed. The process involves a potassium phosphate-catalyzed Erlenmeyer reaction of aromatic aldehydes with hippuric acid followed by an oxazolone ring-opening methanolysis. This process afforded a good overall yield and an excellent product quality via a simple workup. (C) 2009 Elsevier Ltd. All rights reserved.
引用
收藏
页码:625 / 628
页数:4
相关论文
共 19 条
[1]   Enantiodivergent synthesis of cyclobutyl-(Z)-α,β-dehydro-α-amino acid derivatives from (-)-cis-pinononic acid [J].
Aguado, GP ;
Moglioni, AG ;
Ortuño, RM .
TETRAHEDRON-ASYMMETRY, 2003, 14 (02) :217-223
[2]  
ARENAL I, 1981, AN QUIM C-ORG BIOQ, V77, P56
[3]  
ERLENMEYER E, 1893, LIEBIGS ANN CHEM, P275
[4]   SUBSTITUTED PHENYLALANINES AND PHENYLETHYLAMINES [J].
FENNOY, LV .
JOURNAL OF ORGANIC CHEMISTRY, 1961, 26 (11) :4696-&
[5]  
Karade NN, 2005, J CHEM RES, P46
[6]  
KENNEDY N, SUBSTITUENT IN PRESS
[7]   UNUSUAL AMINO-ACIDS .1. ASYMMETRIC-SYNTHESIS OF FURYLALANINE DERIVATIVES [J].
KRAUSE, HW ;
WILCKE, FW ;
KREUZFELD, HJ ;
DOBLER, C .
CHIRALITY, 1992, 4 (02) :110-115
[8]  
LI JJ, 2005, NAME REACTIONS HETER, P229
[9]   Synthesis of chiral building blocks for use in drug discovery [J].
Marino, ST ;
Stachurska-Buczek, D ;
Huggins, DA ;
Krywult, BM ;
Sheehan, CS ;
Nguyen, T ;
Choi, N ;
Parsons, JG ;
Griffiths, PG ;
James, IW ;
Bray, AM ;
White, JM ;
Boyce, RS .
MOLECULES, 2004, 9 (06) :405-426
[10]  
Pasha M., 2007, Journal of pharmacology and toxicology, V2, P264, DOI DOI 10.3923/JPT.2007.264.270