Acetoxyacetyl chloride → Acetic acid [cyclohexylmethyl-(2-hydroxyethyl)carbamoyl]-methyl ester

Participants

Reaction Steps

To a solution of 2-(cyclohexylmethylamino)-ethanol (600 mg, 3.8 mmol) in DCM (6 mL) at 0° C. was added DIPEA (588 mg, 4.6 mmol) and then acetoxyacetyl chloride (467 mg, 3.44 mmol) over 5 min. The resulting mixture was warmed to room temperature, stirred overnight under an atmosphere of nitrogen, diluted with DCM and washed successively with 1 N aqueous HCl, saturated NaHCO3, and brine. The organic layer was dried over magnesium sulfate, filtered, and concentrated to yield the title compound (914 mg). (m/z): [M+H]+ calcd for C13H23NO4, 258.16; found, 258.0.

Provenance & Evidence