The facile production of N-methyl amino acids via oxazolidinones

被引：55

作者：

Aurelio, L ^{[1
]}

Brownlee, RTC ^{[1
]}

Hughes, AB ^{[1
]}

Sleebs, BE ^{[1
]}

机构：

[1] La Trobe Univ, Dept Chem, Bundoora, Vic 3083, Australia

来源：

AUSTRALIAN JOURNAL OF CHEMISTRY | 2000年 / 53卷 / 05期

关键词：

oxazolidinones; N-methyl amino acids; synthesis; reductive cleavage;

D O I：

10.1071/CH99082

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A range of oxazolidinones derived from N-carbamoyl alpha-amino acids were prepared by an efficient method as key intermediates in the synthesis of N-methyl amino acids and peptides. The method was readily applied to most alpha-amino acids except those with basic side chains. The oxazolidinones were converted by reductive cleavage into N-methyl alpha-amino acids.

引用

页码：425 / 433

页数：9

共 41 条

[11]

EFFENBERGER F, 1986, LIEBIGS ANN CHEM, P314

[12] OPTICALLY-ACTIVE 4-OXAPROLINE DERIVATIVES - NEW USEFUL CHIRAL SYNTHONS DERIVED FROM SERINE AND THREONINE [J].

FALORNI, M ;

CONTI, S ;

GIACOMELLI, G ;

COSSU, S ;

SOCCOLINI, F .

TETRAHEDRON-ASYMMETRY, 1995, 6 (01) :287-294

[13] Optical-active N-monomethyl-derivative from alanine, leucine phenyl-alanine and tyrosine. [J].

Fischer, E ;

Lipschitz, W .

BERICHTE DER DEUTSCHEN CHEMISCHEN GESELLSCHAFT, 1915, 48 :360-378

[14] SYNTHESIS OF 9-FLUORENYLMETHYLOXYCARBONYL-PROTECTED N-ALKYL AMINO-ACIDS BY REDUCTION OF OXAZOLIDINONES [J].

FREIDINGER, RM ;

HINKLE, JS ;

PERLOW, DS ;

ARISON, BH .

JOURNAL OF ORGANIC CHEMISTRY, 1983, 48 (01) :77-81

[15]

GREEN TW, 1991, PROTECTIVE GROUPS OR

[16] IMMONIUM ION BASED SYNTHETIC METHODOLOGY - A NOVEL METHOD FOR THE N-METHYLATION OF DIPEPTIDES AND AMINO-ACID DERIVATIVES VIA RETRO AZA DIELS-ALDER REACTIONS [J].

GRIECO, PA ;

BAHSAS, A .

JOURNAL OF ORGANIC CHEMISTRY, 1987, 52 (26) :5746-5749

[17]

GUNTHER H, 1980, NMR SPECTROSCOPY, P101

[18] AMINO-ACIDS AND PEPTIDES .205. AN ALTERNATIVE ROUTE TO N-ALPHA-METHYLAMINO ACID-DERIVATIVES - SYNTHESIS AND CONFORMATION OF SOME N-ALPHA-ACETYL-N-ALPHA-METHYLAMINO ACID METHYLAMIDES [J].

HLAVACEK, J ;

FRIC, I ;

BUDESINSKY, M ;

BLAHA, K .

COLLECTION OF CZECHOSLOVAK CHEMICAL COMMUNICATIONS, 1988, 53 (11A) :2473-2494

[19] TETRAPEPTIDE CCK-A AGONISTS - EFFECT OF BACKBONE N-METHYLATIONS ON IN-VITRO AND IN-VIVO CCK ACTIVITY [J].

HOLLADAY, MW ;

KOPECKA, H ;

MILLER, TR ;

BEDNARZ, L ;

NIKKEL, AL ;

BIANCHI, BR ;

WITTE, DG ;

SHIOSAKI, K ;

LIN, CW ;

ASIN, KE ;

NADZAN, AM .

JOURNAL OF MEDICINAL CHEMISTRY, 1994, 37 (05) :630-635

[20]

ITOH M, 1969, CHEM PHARM BULL, V17, P1679

← 1 2 3 4 5 →