Acetic Anhydride → HCID 178476597, compound

Participants

Reaction Steps

To (cis)-N-((3-chloropyrazin-2-yl)methyl)-4-hydroxycyclohexanecarboxamide (57.4 mmol, 15.47 g) and 4-dimethylaminopyridine (5.74 mmol, 0.701 g) in pyridine (125 ml) at 0° C. was added dropwise acetic anhydride (60.2 mmol, 5.69 ml) and the mixture was stirred at room temperature for one hour. Then the reaction was quenched with 4 N hydrochloric acid to a pH of four and extracted with ethyl acetate three times. The combined organic layers were dried (MgSO4) and concentrated in vacuo. The residue was taken up in toluene and concentrated in vacuo again. The residue was dissolved in dichloromethane (100 ml) and washed with 1 M hydrochloric acid (100 ml). The organic layer was washed with brine, dried (MgSO4) and concentrated in vacuo to give (cis)-4-((3-chloropyrazin-2-yl)methylcarbamoyl)cyclohexyl acetate (16.5 g)

Provenance & Evidence