Dimethylformamide → tert-Butyl carbamate

Participants

Reaction Steps

To a solution of (R)-mandelic acid (100 mg, 0,225 mmol) in DMF (0.5 mL) was added Compound 54 (37.6 mg, 0.247 mmol), followed by BOP reagent (241 mg, 0.545 mmol) and N-methylmorpholine (132 μL, 1.20 mmol) at 0° C. The mixture was stirred at RT for 16 h. DMF was removed in vacuo and the residue dissolved in EtOAC, washed with saturated aq. NaHCO3 and then with brine. The organic layer was separated, dried (MgSO4) and concentrated in vacuo and the residue purified by silica gel chromatography, eluting with 99:1:0.1 to 91.5:8.5:0.85 CH2Cl2 :CH3OH:aq. NH4OH to afford Compound 377 (94 mg, 72%) as a white solid.

Provenance & Evidence