Ethyl chloroformate → HCID 69584952, compound

Participants

Reaction Conditions

Reaction Steps

To an ice cold reaction mixture containing compound 108 (0.17 g, 0.5 mmol) and TEA (0.07 mL, 0.5 mmol) in dichloromethane (5 mL) was added ethyl chloroformate (0.025 mL, 0.5 mmol). The resulting mixture was stirred at 0° C. for 30 min and then at room temperature for 1. After concentration, the residue was partitioned with 10% citric acid and ethyl acetate. The organic phase was separated and dried over MgSO4. After removing the solvent under reduced pressure, the resulting residue was treated with 50% trifluoroacetic acid in dichloromethane at room temperature for 30 min. Removal of the solvent and purification by reverse phase preparative HPLC afford 73 mg of a 1:1 mixture of the title compounds 123 and 124. 1H NMR (CD3OD, 400 MHz): 1.35 (q, 3H), 1.46 (d, 3H), 2.98 (dd, 2H), 3.80 (d, 3H), 4.28 (q, 4H), 6.60–6.98 (m, 3H). MS (ESI) m/z 313.25 (M+H+).

Provenance & Evidence