Dicyclohexylcarbodiimide → Methyl 4-(Acetylamino)-3-[(2,3-Diacetoxypropanoyl)Amino]Benzoate

Participants

Reaction Conditions

Reaction Steps

Compound 16 (0.12 g, 0.57 mmol) was dissolved in a mixture of DMF (2 mL) and dioxane (3 mL) and cooled to 0° C. A solution of 2,3-diacetoxypropionic acid (0.220 g, 1.15 mmol) in dioxane (3 mL) was added followed by the addition of dicyclohexylcarbodiimide (0.195 mL, 0.183 g, 0,870 mmol). The resulting reaction mixture was stirred for 3 hours, initially at 0° C. with slow warming to room temperature. The solid dicyclohexylurea which separated was filtered and the filtrate was concentrated to dryness on a rotary evaporator. The solid residue was filtered and washed on the filter with 5% HCl (5 mL), water (5 mL), 5% NaHCO3 (5 mL), and again with water (2×10 mL). This was dried under vacuum to give 18 (200 mg, 91.3%) as a white solid: mp 130°-134° C.

Provenance & Evidence