(Z)-2-(5-amino-1,2,4-thiadiazol-3-yl)-2-ethoxyiminoacetic acid

Post Date:
Dec 07,2018
Expiry Date:
Dec 07,2019
Detailed Description:
Cas No. :75028-24-9 An improved synthetic route of (Z)-2-(5-amino-1,2,4-thiadiazol-3-yl)-2-(ethoxyimino)acetic acid (2a), an important intermediate for the preparation of Ceftaroline, from N-(3-aminoisoxazol-5-yl)acetamide (8) in total yield of 47% has been developed. The key intermediate (Z)-N-(3-(2-acetamido-1-(ethoxyimino)-2-oxoethyl)-1,2,4-thiadiazol-5- yl)pivalamide (12a) was easily isolated from (Z/E)-N-(3-(2-acetamido-1-(ethoxyimino)-2-oxoethyl)-1,2,4 -thiadiazol-5- yl)pivalamide. The title compound 2a was obtained from the hydrolysis of 12a with a yield of 83%, and its structure was comfirmed by X-ray single crystal diffraction analysis. Moreover, (E)- and (Z)-N-(3-(2-acetamido-1-(ethoxyimino)-2 - oxoethyl)-1,2,4-thiadiazol-5-yl)pivalamide were prepared respectively from the etherification of oxime hydroxyl group under different conditions. This improved procedure has many appealing attributes such as convenient separation, good yields, and easy access to large scale.
CAS Registry Number:
75028-24-9
Synonyms:
;Ceftazidime Norlin Intermediates;ATDE;(Z)-5-Amino-alpha-(ethoxyimino)-1,2,4-thiadiazole-3-acetic acid;
Molecular Formula:
C₆H₈N₄O₃S
Molecular Weight:
216.21452
Molecular Structure:

Offter to Sell