150215-08-0

Upstream product

• 333-20-0 potassium thioacyanate 
• 1885-14-9 phenyl chloroformate 
• 32326-25-3 3-amino-5-methoxyisoxazole 
• 150215-33-1 2-(5-phenoxycarbonylamino-1,2,4-thiadiazol-3-yl)acetaldehyde 
• 67-56-1 methanol 
• 150215-34-2 2-(5-phenoxycarbonylamino-1,2,4-thiadiazol-3-yl)acetic acid 

Relevant academic research and scientific papers

Process for preparing 1,2,4-thiadiazole derivatives

An improved process for the production of 5-amino-1,2,4-thiadiazol-3-yl-(2-(lower)-alkoxyimino)acetic acids starting from 5-substituted- or unsubstituted-3-amino-isoxazole compounds is disclosed herein. The title compounds are useful as acylating agents for the production of 7-acylaminocephalosporins.

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

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)aceta te, which was led to 4.

A Practical Preparation of (Z)-2-(5-Amino-1,2,4-thiadiazol-3-yl)-2-(methoxyimino)acetic Acid

A Z-isomer of 2-(5-amino-1,2,4-thiadiazol-3-yl)-2-(methoxyimino)acetic acid, which is the common acyl moiety of clinically useful cephalosporins, has been prepared from the aminoisoxazols through the thiadiazol-acetate in two pathways.