Lithium Hydroxide → HCID 71679189, compound

Participants

Reaction Steps

Followed general procedure using: the corresponding peptidomimetic epoxide ethyl ester 17b (28 mg, 0.72 mmol); LiOH (1.7 mg, 0.072 mmol); after extraction afforded the desired product as a white solid (20 mg, 77.0%). 1H NMR (MeOD-d4, 400 MHz): δ 7.91 (s, 1H); 7.36-7.31 (m, 1H); 7.07-7.02 (t, 2H); 4.72 (m, 1H); 3.65 (s, 1H); 3.52 (s, 1H); 1.74-1.68 (m, 3H); 1.01-0.99 (d, 6H). 13C NMR (DMSO-d6, 100 MHz): 171.26, 169.20, 165.81, 159.49 (d, J=5.2 Hz), 157.00 (d, J=5.2 Hz), 128.98 (t, J=19.7 Hz); 115.34 (t, J=34.0 Hz); 113.10 (d, J=5.2 Hz), 107.43, 106.22, 52.96, 51.51, 51.32, 41.30, 24.71, 23.81. ESI-HRMS (m/z): [M−H]+ calcd, for C16H20N2O5: 355.3216, observed: 355.3101. HPLC Method 1: Rt=19.7 min, purity=95.0%.

Provenance & Evidence