Dicyclohexylcarbodiimide → HCID 54066929, compound

Participants

Reaction Conditions

Reaction Steps

N,N'-Dicyclohexylcarbodiimide (0.50 g) is added all at once to a solution, cooled to 4° C., of the syn isomer of 2-methoxyimino-2-(2-tritylaminothiazol-4-yl)acetic acid (0.89 g) and 4-(2,2-dimethoxyethyl)-5,6-dioxo-3-thioxo-perhydro-1,2,4-triazine (0.47 g) in dimethylformamide (20 cc); the mixture is stirred for 1 hour at 4° C. and then for 3 hours at 20° C. The reaction suspension is filtered, the filtrate is diluted with ethyl acetate (100 cc), the mixture is washed with water (2×50 cc), a 1% strength solution of sodium bicarbonate (2×50 cc) and a semi-saturated solution of sodium chloride (2×50 cc), dried over sodium sulphate and filtered and the filtrate is concentrated to dryness at 20° C. under 20 mm Hg (2.7 kPa). The residue is triturated in isopropyl ether (10 cc) and, after filtration and drying, the syn isomer of 4-(2,2-dimethoxyethyl)-5,6-dioxo-3-[2-methoxyimino-2-(2-tritylaminothiazol-4-yl)-acetylthio]-1,4,5,6-tetrahydro-1,2,4-triazine (0.91 g) is obtained in the form of a yellow powder.

Provenance & Evidence