Methanol → HCID 66652327, compound

Participants

Reaction Steps

A solution of (S)-benzyl 3-(2-methoxy-2-oxo-1-phenylethyl)-4-oxo-1-phenyl-1,3,8-triazaspiro[4.5]decane-8-carboxylate (2.16 g, 4.21 mmol, 1 equiv.) and lithium hydroxide (353 mg, 8.41 mmol, 2 equiv) in a 4:1 mixture of methanol and water (20 ml t/v) was stirred at ambient temperature for 16 hrs. The reaction was concentrated in vacuo and the mixture was partitioned between ethyl acetate and 10% citric acid. The organic layer was further washed with water and brine, dried over MgSO4, filtered and concentrated. The resulting residue was dried thoroughly to afford (S)-2-(8-(benzyloxycarbonyl)-4-oxo-1-phenyl-1,3,8-triazaspiro[4.5]decan-3-yl)-2-phenylacetic acid as a white solid (2.05 g, quant); 1H NMR (400 MHz, DMSO-d6): δ 1.67 (t, 2H, J=12.4 and 10.4 Hz); 2.25-2.33 (m, 2H); 3.56 (m, 2H); 3.98-4.05 (m, 2H); 4.14 (d, 1H, J=4.4 Hz); 4.86 (d, 1H, J=5.2 Hz); 5.14 (m, 2H); 5.81 (s, 1H); 6.67 (d, 2H, J=7.6 Hz); 6.81 (t, 1H, J=6.8 and 7.6 Hz); 7.17 (dd, 2H, J=7.6 and 7.2 Hz); 7.32-7.45 (m, 10H); 13.5 (s, 1H); MS for C29H29N3O5 m/z 500.21 (M+H)+.

Provenance & Evidence