Solventless Synthesis of N-Protected Amino Acids in a Ball Mill

被引：51

作者：

Konnert, Laure ^{[1
]}

Gauliard, Anne ^{[1
]}

Lamaty, Frederic ^{[1
]}

Martinez, Jean ^{[1
]}

Colacino, Evelina ^{[1
]}

机构：

[1] Univ Montpellier 2, UMR CNRS UM 1 UM 2 5247, IBMM, F-34095 Montpellier 5, France

来源：

ACS SUSTAINABLE CHEMISTRY & ENGINEERING | 2013年 / 1卷 / 09期

关键词：

Amino Acids; Ball mill; Protective groups; Solvent free; E-factor; NUCLEOSIDE; ANALOGS; ESTERS;

D O I：

10.1021/sc4001115

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

An eco-friendly methodology for preparing carbamate N-protected alpha-amino acids is described using ball-milling technology. Some beta-amino acids were also investigated in this study. This solvent-free methodology gave Boc-, Z-, and Fmoc-N-protected compounds in good to excellent yields with improved environmental impact compared to classical syntheses in solution. Different planetary ball mills were employed. The results are also discussed according to the different process parameters (grinding material, number of balls, rotation speed).

引用

页码：1186 / 1191

页数：6

共 34 条

[21]

Matlack A. S., 2001, Introduction to Green Chemistry

[22] Mechanosynthesis of amides in the total absence of organic solvent from reaction to product recovery [J].

Metro, Thomas-Xavier ;

Bonnamour, Julien ;

Reidon, Thomas ;

Sarpoulet, Jordi ;

Martinez, Jean ;

Lamaty, Frederic .

CHEMICAL COMMUNICATIONS, 2012, 48 (96) :11781-11783

[23] Preparation of Chiral Amino Esters by Asymmetric Phase-Transfer Catalyzed Alkylations of Schiff Bases in a Ball Mill [J].

Nun, Pierrick ;

Perez, Violaine ;

Calmes, Monique ;

Martinez, Jean ;

Lamaty, Frederic .

CHEMISTRY-A EUROPEAN JOURNAL, 2012, 18 (12) :3773-3779

[24] Application of ball milling technology to carbohydrate reactions: I. Regioselective primary hydroxyl protection of hexosides and nucleoside by planetary ball milling [J].

Patil, Premanand Ramrao ;

Kartha, K. P. Ravindranathan .

JOURNAL OF CARBOHYDRATE CHEMISTRY, 2008, 27 (05) :279-293

[25] Synthesis of nucleoside analogues in a ball mill: fast, chemoselective and high yielding acylation without undesirable solvents [J].

Ravalico, Francesco ;

James, Stuart L. ;

Vyle, Joseph S. .

GREEN CHEMISTRY, 2011, 13 (07) :1778-1783

[26] The Suzuki-Miyaura Reaction under Mechanochemical Conditions [J].

Schneider, Franziska ;

Stolle, Achim ;

Ondruschka, Bernd ;

Hopf, Henning .

ORGANIC PROCESS RESEARCH & DEVELOPMENT, 2009, 13 (01) :44-48

[27] Atom efficiency and catalysis in organic synthesis [J].

Sheldon, RA .

PURE AND APPLIED CHEMISTRY, 2000, 72 (07) :1233-1246

[28] Solventless protocol for efficient bis-N-boc protection of adenosine, cytidine, and guanosine derivatives [J].

Sikchi, Siddharth A. ;

Hultin, Philip G. .

JOURNAL OF ORGANIC CHEMISTRY, 2006, 71 (16) :5888-5891

[29] Ball milling in organic synthesis: solutions and challenges [J].

Stolle, Achim ;

Szuppa, Tony ;

Leonhardt, Silke E. S. ;

Ondruschka, Bernd .

CHEMICAL SOCIETY REVIEWS, 2011, 40 (05) :2317-2329

[30] Solvent-free organic synthesis [J].

Tanaka, K ;

Toda, F .

CHEMICAL REVIEWS, 2000, 100 (03) :1025-1074

← 1 2 3 4 →