Practical Preparation of (Z)-2-(5-Amino-1,2,4-thiadiazol-3-yl)-2-methoxyiminoacetic Acid: A Side-Chain of the Fourth Generation of Cephem Antibiotics

Autor:	Yasuyuki Kurita, Takashi Inagaki, Tetsuro Tamai, Hiroki Gunji, Ryonosuke Yoshida, Kuniaki Tatsuta, Shozo Miura
Rok vydání:	1994
Předmět:	Cephem Barium oxide medicine.drug_class Antibiotics General Chemistry Medicinal chemistry Dimethyl sulfate chemistry.chemical_compound Acetic acid chemistry Side chain medicine Moiety Methyl iodide
Zdroj:	Bulletin of the Chemical Society of Japan. 67:1701-1707
ISSN:	1348-0634 0009-2673
Popis:	A Z-isomer (4) of 2-(5-amino-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 2-(5-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 from 3-aminoisoxazole (10). Also, O-methylation of 2-hydroxyimino-2-(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 was found to afford exclusively the desired Z-isomer (14a) of methyl 2-(5-methoxycarbonylamino-1,2,4-thiadiazol-3-yl)-2-(methoxyimino)acetate, which was led to 4.
Databáze:	OpenAIRE
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