Pyridine → HCID 57947471, compound

Participants

Reaction Steps

To a solution of (S)-methyl 4-(tert-butoxycarbonyl(methyl)amino)-5-(tert-butyldimethylsilyloxy)pentanoate (111 mmol) and pyridine (150 mL, 1.662 mol) in THF (500 mL) was added acetyl chloride (150 mL, 333.2 mmol) at 0° C. The resulting mixture was stirred at RT for 1 h. The solvent was removed and the remaining residue was diluted with EtOAc. The organic mixture was washed with water and brine, dried over Na2SO4, filtered, and concentrated. The residue was purified on silica gel column to give (S)-4-(tert-butoxycarbonylamino)-5-(tert-butyldimethylsilyloxy)pentyl acetate (39.6 g, 95%). LRMS (M+H+-Boc) m/z 276.2.

Provenance & Evidence