Sodium Hydroxide → N-[2(S)-(t-Butoxycarbonylamino)-3(S)-methylpentyl]-N-(1-naphthylmethyl)glycine

Participants

Reaction Steps

N-[2(S)-(t-Butoxycarbonylamino)-3(S)-methylpentyl]-N-(1-naphthylmethyl)glycine methyl ester (7, 2.61 g, 6.10 mmol) was dissolved in MeOH (50 ml) and 1N NaOH (24.4 ml, 24.4 mmol) was added. The mixture was stirred at ambient temperature for 4 h and concentrated. The resulting residue was dissolved in water (25 ml) and neutralized with 1N HCl (24.4 ml). The aqueous layer was washed with EtOAc (3×50 ml). The organic layers were combined, dried with Na2SO4, filtered, and concentrated to give the product. 1H NMR (CD3OD) δ 8.43 (1H, d, J=6 Hz), 7.97 (2H, t, J=6 Hz) 7.75-7.48 (4H, m), 4.96 (1H, d, J=12 Hz), 4.72 (1H, d, J=12 Hz), 3.80-3.58 (3H, m), 3.49-3.40 (1H, dd,, J=3 and 12 Hz), 3.03 (1H, dd, J=3 and 12 Hz), 1.42 (9H, s,), 1.37-1.28 (2H, m), 1.80-1.00 (1H, m), 0.94-0.78 (6H, m,) ppm.

Provenance & Evidence