Hydrochloric Acid → 3-Acetoxymethyl-7-[2-(2-tritylamino-4-thiazolyl)-2-methoxyiminoacetamido]-3-cephem-4-carboxylic acid

Participants

Reaction Steps

576.5 g of the syn isomer of 2-(2-tritylamino-4-thiazolyl)-2-methoxyimino-acetic acid were added at 0° C. to a solution of 247.8 g of tosyl chloride in 780 m. of dimethylformamide and then 196 ml of triethylamine were added thereto. The mixture was held at 0° C. while adding thereto a solution of 272 g of 7-amino-cephalosporanic acid in 3 liters of ethylene chloride and 450.7 ml of triethylamine cooled to -70° to -75° C. and the mixture was held at -20° C. for 30 minutes. Then 270 ml of acetic acid followed by 540 ml of demineralized water were added thereto and the temperature rose to -15° to -20° C. 11 liters of demineralized water were added thereto and the pH was adjusted to 1 to 1.2 by addition of 0.1N hydrochloric acid. The decanted organic phase was washed 3 times with 2700 ml of demineralized water and was concentrated under reduced pressure in a bath at 8° to 30° C. to a volume of 1350 ml to obtain a solution of syn isomer of 3-acetoxymethyl-7-[2-(2-tritylamino-4-thiazolyl)-2-methoxyimino-acetamido]-ceph-3-eme-4-carboxylic acid.

Provenance & Evidence