Ethyl chloroformate → HCID 67125951, compound

Participants

Reaction Conditions

Reaction Steps

To a stirred solution of 5-(1,2,2,6,6-pentamethylpiperidin-4-yloxy)picolinic acid (250 mg, 0.86 mmol) in DCM/THF (6 mL, 2:1, v/v) at rt was added TEA (144 μL, 1.03 mmol) and ethyl chloroformate (82 μL, 0.86 mmol). The resulting mixture was stirred at rt for 20 min before tert-butyl 4-aminophenylcarbamate (178 mg, 0.86 mmol) was added. The resulting mixture was heated at 50° C. for 1 h. LC-MS indicated the reaction was complete. Solvents were then removed under reduced pressure and the residue was partitioned between EtOAc (30 mL) and brine (20 mL). The organic layer was dried over MgSO4, filtered, and concentrated under reduced pressure to give crude tert-butyl 4-(5-(1,2,2,6,6-pentamethylpiperidin-4-yloxy)picolinamido)phenylcarbamate (500 mg) as an off-white foam. LC-MS (ESI) m/z 483 (M+H)+.

Provenance & Evidence