Esterification of Unprotected α-Amino Acids in Ionic Liquids as the Reaction Media

被引：10

作者：

Biondini, Daniele ^{[1
]}

Brinchi, Lucia ^{[1
]}

Germani, Raimondo ^{[1
]}

Goracci, Laura ^{[1
]}

Savelli, Gianfranco ^{[1
]}

机构：

[1] Univ Perugia, Dipartimento Chim, CEMIN, I-06123 Perugia, Italy

来源：

LETTERS IN ORGANIC CHEMISTRY | 2010年 / 7卷 / 01期

关键词：

Ionic liquid; esterification; amino acids; nucleophilic substitution;

D O I：

10.2174/157017810790533940

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Ionic liquid 1,3-dimethylimidazolium methanesulfonate was used to prepare amino acids benzylic esters from unprotected amino acids and benzyl chloride. Esterification of several amino acids was achieved with satisfactory yields: by-products can be removed by a simple work-up procedure to afford the pure product. The described method is simple, mild, rapid and save.

引用

页码：39 / 44

页数：6

共 36 条

[1] A SIMPLE AND CONVENIENT METHOD FOR ESTERIFICATION OF TRYPTOPHAN AND OTHER AMINO-ACIDS [J].

ARAI, I ;

MURAMATSU, I .

JOURNAL OF ORGANIC CHEMISTRY, 1983, 48 (01) :121-123

[2] An effective chemoselective esterification of hydroxybenzoic acids in ionic liquid promoted by KF [J].

Biondini, D ;

Brinchi, L ;

Germani, R ;

Savelli, G .

LETTERS IN ORGANIC CHEMISTRY, 2006, 3 (03) :207-211

[3]

Bodanszky M., 1984, The Practice of Peptide Synthesis

[4] Ionic liquids as reaction media for esterification of carboxylate sodium salts with alkyl halides [J].

Brinchi, L ;

Germani, R ;

Savelli, G .

TETRAHEDRON LETTERS, 2003, 44 (10) :2027-2029

[5] Efficient esteritication of carboxylic acids with alkyl halides catalyzed by fluoride ions in ionic liquids [J].

Brinchi, L ;

Germani, R ;

Savelli, G .

TETRAHEDRON LETTERS, 2003, 44 (35) :6583-6585

[6] A simple and practical method for the preparation and purity determination of halide-free imidazolium ionic liquids [J].

Cassol, CC ;

Ebeling, G ;

Ferrera, B ;

Dupont, J .

ADVANCED SYNTHESIS & CATALYSIS, 2006, 348 (1-2) :243-248

[7] Ionic liquids: solvent properties and organic reactivity [J].

Chiappe, C ;

Pieraccini, D .

JOURNAL OF PHYSICAL ORGANIC CHEMISTRY, 2005, 18 (04) :275-297

[8] Reactivity of ionic liquids [J].

Chowdhury, Shahana ;

Mohan, Ram S. ;

Scott, Janet L. .

TETRAHEDRON, 2007, 63 (11) :2363-2389

[9]

COPPOLA GM, 1997, ASYMMETRIC SYNTHESIS

[10] Ionic liquid (molten salt) phase organometallic catalysis [J].

Dupont, J ;

de Souza, RF ;

Suarez, PAZ .

CHEMICAL REVIEWS, 2002, 102 (10) :3667-3691

← 1 2 3 4 →