Synthesis of (Z)-2-(2-formamido-4-thiazolyl)-2-(substituted alkoxyimino) acetic acids.
(Z)-2-(2-formamido-4-thiazolyl)-2-(substituted alkoxyimino) acetic acids were synthesized by a new method based on the following sequence of reactions: treatment of the tert-butyl acetoacetate with sodium nitrite, alkylation of the oxime formed with an appropriate alkyl halide, halogenation of methyl alpha-keto group and simultaneous cleavage of tert-butyl ester with sulfuryl chloride, protection of the obtained acid function with diphenyldiazomethane, formation of the 2-aminothiazole ring by the Hantzsch method with thiourea, formylation of the amino group and selective final cleavage of the diphenylmethyl ester by treatment with trifluoroacetic acid and anisol. The developed procedure allows the synthesis of (Z)-2-(2-formamido-4-thiazolyl)-2-(substituted alkoxyimino) acetic acids, with an ester function in the alkoxyimino group employing a simple method and obtaining higher yields in comparison with the habitually used classic method.
López
M
M
Department of Chemical Synthesis, Center of Pharmaceutical Chemistry, La Habana, Cuba.
Rodríguez
Z
Z
González
M
M
Valdés
B
B
Vélez
H
H
Fini
A
A
D000085:Acetates / Q000138:chemical synthesis* / Q000737:chemistry; D002855:Chromatography, Thin Layer; D009682:Magnetic Resonance Spectroscopy
D000085:Acetates