Formamide → HCID 131713362, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 255 mg of 3-azidomethyl-7-amino-ceph-3-eme-4-carboxylic acid and 3 ml of anhydrous formamide was stirred for 15 minutes and then 168 mg of triethylenediamine were added in fractions. 412 mg of pyridine hydroiodide were added to the resulting solution and after cooling the mixture to 15° C., 532 mg of 2-(2-tritylamino-4-thiazolyl)-2-(2-aminoiminomethylthioethoxyimino)-acetic acid, 207 mg of pyridine hydroiodide and 3 ml of dimethylformamide were added all at once to the mixture. 412 mg of dicyclohexylcarbodiimide were added to the mixture which was stirred at 15° C. for 20 minutes, at 20° C. for 40 minutes and was then vacuum filtered. 100 ml of water were added to the filtrate and the mixture was stirred for 30 minutes, let stand for 30 minutes and was then vacuum filtered. The recovered product was washed with water and dried to obtain 437 mg of raw product which was stirred with 8.6 ml of chloroform for 30 minutes. The mixture was vacuum filtered and the filtrate was treated with activated carbon and was vacuum filtered. The filtrate was evaporated to dryness to obtain 350 mg of internal salt of syn isomer of 3-azidomethyl-7-[2-(2-tritylamino-4-thiazolyl)-2-(2-aminoiminomethylthioethoxyimino)-acetamido]-ceph-3-eme-4-carboxylic acid.

Provenance & Evidence