Facile and rapid regeneration of free amino acids from N-benzyloxycarbonyl-5-oxazolidinones and from N-benzyloxycarbonylamino derivatives by treatment with BCl3 in dichloromethane

被引：6

作者：

Allevi, P

Cribiù, R

Anastasia, M

机构：

[1] Univ Milan, Dipartimento Med Chirurg & Odontoiatria, I-20142 Milan, Italy

[2] Univ Milan, Dipartimento Chim Biochim & Biotecnol Med, I-20133 Milan, Italy

来源：

TETRAHEDRON LETTERS | 2004年 / 45卷 / 30期

关键词：

N-benzyloxycarbonyl-5-oxazolidinones; N-benzyloxycarbonylamino; acids derivatives;

D O I：

10.1016/j.tetlet.2004.06.011

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Reaction of benzyloxycarbonyl-5-oxazolidinones and of N-benzyloxycarbonylamino acids with BCl3 in dichloromethane at room temperature affords the corresponding free amino acids. (C) 2004 Elsevier Ltd. All rights reserved.

引用

页码：5841 / 5843

页数：3

共 19 条

[1] Mild regeneration of the carboxylic group of amino acid alkyl esters by aqueous methanolic sodium hydrogen carbonate via 5-oxazolidinones [J].

Allevi, P ;

Anastasia, M .

TETRAHEDRON LETTERS, 2003, 44 (41) :7663-7665

[2] Cleavage of benzyloxycarbonyl-5-oxazolidinones to α-benzyloxycarbonylamino-α-alkyl esters by alcohols and sodium hydrogen carbonate [J].

Allevi, P ;

Cighetti, G ;

Anastasia, M .

TETRAHEDRON LETTERS, 2001, 42 (31) :5319-5321

[3] AN IMPROVED SYNTHESIS OF L-HOMOHISTIDINE [J].

ALTMAN, J ;

WILCHEK, M ;

LIPP, R ;

SCHUNACK, W .

SYNTHETIC COMMUNICATIONS, 1989, 19 (11-12) :2069-2076

[4] The facile production of N-methyl amino acids via oxazolidinones [J].

Aurelio, L ;

Brownlee, RTC ;

Hughes, AB ;

Sleebs, BE .

AUSTRALIAN JOURNAL OF CHEMISTRY, 2000, 53 (05) :425-433

[5] REACTION OF ACYLAMINO ACIDS WITH PARAFORMALDEHYDE [J].

BENISHAI, D .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1957, 79 (21) :5736-5738

[6] A novel, one-pot preparation of N-methyl-α-amino acid dipeptides from oxazolidinones and amino acids [J].

Dorow, RL ;

Gingrich, DE .

TETRAHEDRON LETTERS, 1999, 40 (03) :467-470

[7] REACTIONS OF BORON TRICHLORIDE WITH ORGANIC COMPOUNDS [J].

GERRARD, W ;

LAPPERT, MF .

CHEMICAL REVIEWS, 1958, 58 (06) :1081-1111

[8]

GREEN TW, 1991, PROTECTIVE GROUPS OR, P266

[9] SULFUR-CONTAINING POLYPEPTIDES .14. REMOVAL OF BUTYLOXYCARBONYL GROUP WITH BORON TRIFLUORIDE ETHERATE [J].

HISKEY, RG ;

BEACHAM, LM ;

MATL, VG ;

SMITH, JN ;

WILLIAMS, EB ;

THOMAS, AM ;

WOLTERS, ET .

JOURNAL OF ORGANIC CHEMISTRY, 1971, 36 (03) :488-&

[10]

HO TL, 1986, J ORG CHEM, P2405

← 1 2 →