Hydrochloric Acid → HCID 18660170, compound

Participants

Reaction Steps

N-[(t-Butyloxycarbonyl)-pyrrolidin-2(S)-ylmethyl]-(N-2-methylbenzyl)-glycine methyl ester (41.85 g, 0.111 mol) was dissolved in CH3OH (300 mL) at 0° C. and treated with 2 N NaOH solution (111 mL, 0.222 mol) and allowed to stir at ambient temperature for 3 hr. 1 N HCl (235 mL, 0.235 mol) was added, the CH3OH was removed on a rotary evaporator, and the residue was extracted with EtOAc (2×1.5 L), washed with brine, and dried (MgSO4). Filtration and concentration to dryness gave the title compound as a white solid. 1H NMR (CD3OD ) δ 7.56 (d, 1H, J=7.5 Hz), 7.15-7.36 (m, 3H), 4.70 (d, 1H, J=13 Hz), 4.27 (d, 1H, J=13 Hz), 4.1-4.2 (m, 1H), 3.73 (d, 1H, J=16 Hz), 3.59 (d, 1H, J=16 Hz), 3.15-3.5 (m, 4H), 2.49 (s, 3H), 2.1-2.2 (m, 1H), 1.7-1.9 (m, 2H), 1.6-1.7 (m, 1H), 1.46 (s, 9 h).

Provenance & Evidence