Lithium Hydroxide → HCID 71817935, compound

Participants

Reaction Steps

Synthesized following general saponification procedure using the following quantities: the corresponding peptidomimetic epoxide ethyl ester 18b (51.6 mg, 0.1 mmol); LiOH (5 mg, 0.2 mmol); MeOH/H2O (1.5 mL: 0.5 mL: 0.5 mL): yielded 29 as a white solid (26.2 mg, 54.2%). 1H NMR (MeOD-d4, 400 MHz): δ 7.62 (s. 1H); 6.93 (s, 1H); 6.87 (s, 2H); 4.84-4.82 (m, 1H); 3.53-3.49 (d, 1H); 3.38-3.35 (d, 1H); 3.25-3.22 (m, 2H); 2.25 (s, 3H); 2.07 (s, 6H). 13C NMR (MeOD-d4, 100 MHz): 174.40, 172.62, 170.80, 168.89, 136.54, 135.74, 135.11, 133.43, 131.25, 128.18, 117.26, 54.20, 53.82, 53.69, 52.80, 29.34, 19.55, 16.86. ESI-HRMS (m/z): [M−H+] calcd. for C19H22N4O5: 385.1517, observed: 385.1516. HPLC Method 2: Rt=16.4 min, purity=95.4%.

Provenance & Evidence