Lithium Hydroxide → HCID 71818387, compound

Participants

Reaction Steps

Followed general procedure using: the corresponding peptidomimetic epoxide ethyl ester 17c (85 mg, 0.22 mmol); LiOH (5.2 mg, 0.22 mmol); after extraction afforded the desired product as a white solid (59 mg, 74.8%). 1H NMR (DMSO-d6, 400 MHz): δ 9.88 (s, 1H); 8.81-8.79 (d, 1H, J=8.21 Hz); 7.38-7.33 (m, 1H); 7.17-7.13 (t, 2H); 4.61-4.56 (q, 1H); 3.70-3.69 (d, 1H, J=1.79 Hz); 3.52-3.51 (d, 1H, J=1.79 Hz); 1.66-1.58 (m, 3H); 0.93-0.88 (dd, 6H). 13C NMR (DMSO-d6, 100 MHz): 171.35, 169.20, 165.79, 159.48 (d, J=5.16 Hz); 157.01 (d, J=5.21 Hz); 128.58 (t, 19.7 Hz); 114.63 (t, J=34.0 Hz); 112.39 (d, J=22.6 Hz); 53.05, 51.71, 51.62, 41.32, 24.71, 21.96. ESI-HRMS (m/z): [M−H]+ calcd. for C16H20N2O5: 355.3216, observed: 355.3201. HPLC Method 1: Rt=18.9 min, purity=96.5%.

Provenance & Evidence