HCID 59309441, compound → HCID 57583234, compound

Participants

Reaction Steps

3-Allylcarbamoyl-5-amino-2,4,6-triiodo-benzoyl chloride (7) (20 g, 32.4 mmol) was dissolved in dry DMA (50 mL) and threonic acid chloride triacetate (18) (18.22 g, 64.8 mmol) was added. The reaction was stirred for 3 days at room temperature with nitrogen bubbling through. The reaction mixture was diluted with ethyl acetate (100 mL) and washed with ice-water (5×20 mL). The organics were collected, dried over MgSO4, filtered and evaporated to dryness under reduced pressure. The solid was adsorbed onto silica gel and purified by column chromatography eluting with DCM: ethyl acetate (0-100%, SiO2, 750 g, 10 CV) to give acetic acid 2,3-diacetoxy-1-(3-allylcarbamoyl-5-chlorocarbonyl-2,4,6-triiodo-phenylcarbamoyl)-propyl ester as a yellow solid (15.1 g, 54%).

Provenance & Evidence