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Titolo:
PRACTICAL PREPARATION OF -AMINO-1,2,4-THIADIAZOL-3-YL)-2-METHOXYIMINOACETIC ACID - A SIDE-CHAIN OF THE 4TH GENERATION OF CEPHEM ANTIBIOTICS
Autore:
TATSUTA K; MIURA S; GUNJI H; TAMAI T; YOSHIDA R; INAGAKI T; KURITA Y;
Indirizzi:
WASEDA UNIV,GRAD SCH SCI & ENGN,3-4-1 OHKUBO,SHINJUKU KU TOKYO 169 JAPAN KATAYAMA SEIYAKUSYO CO LTD HIRAKATA 573 JAPAN KEIO UNIV,DEPT APPL CHEM,KOHOKU KU YOKOHAMA KANAGAWA 223 JAPAN
Titolo Testata:
Bulletin of the Chemical Society of Japan
fascicolo: 6, volume: 67, anno: 1994,
pagine: 1701 - 1707
SICI:
0009-2673(1994)67:6<1701:PPO->2.0.ZU;2-K
Fonte:
ISI
Lingua:
ENG
Soggetto:
CEPHALOSPORINS; SERIES;
Tipo documento:
Article
Natura:
Periodico
Settore Disciplinare:
Science Citation Index Expanded
Citazioni:
11
Recensione:
Indirizzi per estratti:
Citazione:
K. Tatsuta et al., "PRACTICAL PREPARATION OF -AMINO-1,2,4-THIADIAZOL-3-YL)-2-METHOXYIMINOACETIC ACID - A SIDE-CHAIN OF THE 4TH GENERATION OF CEPHEM ANTIBIOTICS", Bulletin of the Chemical Society of Japan, 67(6), 1994, pp. 1701-1707

Abstract

A Z-isomer (4) of mino-1,2,4-thiadiazol-3-yl)-2-(methoxyimino)acetic acid, which is the common acyl moiety of clinically useful cephem antibiotics, has been prepared from the aminoisoxazoles through the skeletal rearrangement in several routes. Reaction of 3-amino-5-methoxyisoxazole (7) with alkoxycarbonyl isothiocyanates gave methyl alkoxycarbonylamino-1,2,4-thiadiazol-3-yl)acetates (8), which were converted into the target compound 4 through the reaction of the corresponding keto ester with O-methylhydroxylamime. Compound 4 was prepared similarly from3-aminoisoxazole (10). Also, O-methylation of (5-methoxycarbonylamino-1,2,4-thiazol-3-yl)acetate (15) with methyl iodide or dimethyl sulfate in the presence of barium oxide and barium hydroxide octahydrate wasfound to afford exclusively the desired Z-isomer (14a) of methyl no-1,2,4-thiadiazol-3-yl)-2-(methoxyimino)acetate, which was led to 4.

ASDD Area Sistemi Dipartimentali e Documentali, Università di Bologna, Catalogo delle riviste ed altri periodici
Documento generato il 03/12/20 alle ore 21:49:56