Hydrochloric Acid → HCID 131712371, compound

Participants

Reaction Steps

4.7 g of the product of Step B were added to 70 ml of methylene chloride and then 70 ml of distilled water were added thereto. 21 ml of trithylamine were added thereto with stirring and under reduced pressure and after 5 minutes of stirring, 15.3 ml of tert.-butyl bromoacetate were added thereto all at once. The mixture was vigorously stirred at 25°-30° C. for 30 minutes and was then acidified at 15°-20° C. by addition of 8 ml of hydrochloric acid. The decanted aqueous phase was extracted twice with 20 ml of methylene chloride and the combined organic phases were washed 3 times with 50 ml of distilled water, was dried over magnesium sulfate and was vacuum filtered. The filtrate was rinsed and the filtrate was evaporated to dryness under reduced pressure. The 9.8 g of gum were dissolved in 30 ml of ethyl acetate and the mixture was stirred at 20° C. until dissolution occured. 0.75 ml of diethylamine were added thereto followed by the addition of 60 ml of isopropyl ether and the mixture was stirred at 20°-25° C. for 15 minutes and was then vacuum filtered. The recovered product was washed twice with 5 ml of a 1-2 ethyl acetate-isopropyl ether mixture and 3 times with 10 ml of isopropyl ether and was dried to obtain 4.31 g of the syn isomer of diethylamine 3-methyl-7-[2-(2-tritylamino-4-thiazolyl)-2-(tert.-butoxycarbonylmethoxyimino)-acetamido]-ceph-3-eme-4-carboxylate melting at 140° C. (decomposition).

Provenance & Evidence