Lithium Hydroxide → HCID 71817936, compound

Participants

Reaction Steps

Synthesized following general saponification procedure using the following quantities: the corresponding peptidomimetic epoxide ethyl ester 19a (112 mg, 0.28 mmol); LiOH (6.9 mg, 0.29 mmol); THF/MeOH/H2O (2.5 mL: 1.0 mL: 1.0 mL); yielded 32 as a white solid (45 mg, 43.3%). 1H NMR (MeOD-d4, 400 MHz): δ 8.97 (s, 1H); 7.52-7.50 (d, 2H); 7.32 (s, 1H); 7.30-7.26 (t, 3H); 4.94-4.92 (t, 1H): 3.62 (s, 1H); 3.52-3.45 (q, 2H); 3.43 (s, 1H). 13C NMR (DMSO-d6, 100 MHz): 172.48, 169.65, 168.87, 153.83, 152.41, 138.16, 128.33, 124.04, 120.73, 115.89, 54.49, 53.60, 52.89 32.87. ESI-HRMS (m/z): [M+H+] calcd. for C16H15N3O5S: 360.0660, observed: 360.0673; HPLC method 2: Rt=16.4 min; Purity: 95.2%.

Provenance & Evidence