Lithium Hydroxide → HCID 71679021, compound

Participants

Reaction Steps

Followed general procedure using: the corresponding peptidomimetic epoxide ethyl ester 17d (203 mg, 0.45 mmol); LiOH (10.8 mg, 0.45 mmol); after extraction afforded the desired product as a white solid (150 mg, 78.8%). 1H NMR (DMSO-d6, 400 MHz): δ 12.51 (bs, 1H); 8.64-8.61 (d, 1H, J=12.0 Hz); 7.95-7.92 (t, 2H); 7.62 (s, 1H); 7.28-7.24 (t, 2H); 4.63-4.58 (m, 1H); 3.51-3.50 (d, 1H, J=1.60 Hz); 3.34-3.33 (d, 1H, J=1.60 Hz); 165-1.54 (m, 3H); 0.91-0.88 (t, 6H). 13C NMR (MeOD-d4, 100 MHz): 172.44, 165.32, 162.87, 159.37, 150.45, 132.60, 132.57, 129.14, 129.06, 116.56, 116.34, 108.69, 54.41, 53.55, 53.19, 41.79, 26.21, 23.54, 22.02. ESI-HRMS (m/z): [M+H+] calcd. for C19H20FN3O5S: 422.1180, observed: 422.1188. HPLC Method 1: Rt=24.6 min, purity=95.7%.

Provenance & Evidence