Diisopropyl Ether → tert-butyl 2-[(Z)-[1-(5-amino-1,2,4-thiadiazol-3-yl)-2-chloro-2-oxoethylidene]amino]oxy-2-methylpropanoate;hydrochloride

Participants

Reaction Steps

To a solution of phosphorus pentachloride (11.11 g) in methylene chloride (167.8 ml) was added (Z)-2-(5-amino-1,2,4-thiadiazol-3-yl)-2-(1-tert-butoxycarbonyl-1-methylethoxyimino)acetic acid (16.78 g) at -20° C. The resultant mixture was stirred at -20° to -10° C. for 1.5 hours, and to the mixture was added dropwise diisopropyl ether (671.2 ml) at -20° to -10° C. The mixture was stirred under ice-cooling for 1 hour and the resultant precipitate was collected by filtration to give (Z)-2-(5-amino-1,2,4-thiadiazol-3-yl)-2-(1-tert-butoxycarbonyl-1-methylethoxyimino)acetyl chloride hydrochloride (14.8 g).

Provenance & Evidence