Hydrochloric Acid → HCID 53722240, compound

Participants

Reaction Steps

8.28 g of pure potassium carbonate were added under argon to a mixture of 9.88 g of the hydrochloride of ethyl 2-(2-tritylamino-4-thiazolyl)-2-hydroxyimino-acetate in 25 ml of dry dimethylformamide and the mixture was stirred for 15 minutes and was then cooled for 10 minutes on a methanol-ice bath. 11.2 ml of ethyl bromoacetate was added dropwise over 5 minutes and spontaneous heating occured with stirring under an inert atmosphere. The mixture was poured into a mixture of 400 ml of water and 80 ml of ethyl acetate and the mixture was stirred and decanted. The organic phase was washed twice with 80 ml of water and the aqueous phase was extracted with 80 and 50 ml of ethyl acetate. The organic phase was dried and vacuum filtered. The filter was rinsed and the filtrate was evaporated to dryness. The residue was taken up in ether and the mixture was stirred while crystallization occured. The mixture was vacuum filtered and the product was rinsed with ether and dried to obtain 7.54 g of syn isomer of ethyl 2-(2-tritylamino-4-thiazolyl)-2-(ethylcarboxymethyloxyimino)-acetate melting at 154° C.

Provenance & Evidence