Triethylamine → HCID 73294497, compound

Participants

Reaction Conditions

Reaction Steps

In a four necked round bottom flask, Et3N (5.5 mL, 39.4 mmol) was added to a solution of (2R,3S)-3-hydroxy-2-{[(4-phenylbutoxy)carbonyl]amino}butanoic acid (3.9 g, 13.1 mmol) in dry CH2Cl2 (170 mL) under argon. After cooling at 0° C., HBTU (7.5 g, 19.7 mmol) was added and the mixture stirred 3 h at 0° C., then 3.5 h at rt. The obtained solid was filtered-off and the solvent removed under vacuum. The crude was purified by typical silica gel automatic column chromatography, eluting with Cy/AcOEt (from 95:5 to 60:40). The resulting pale yellow oil (0.61 g) was further crystallized from cyclohexane to afford the pure title compound, (0.23 g, 6%), as white solid. MS (ESI) m/z: 276.24 [M−H]−. FTIR (cm−1): 3312, 3060, 3026, 2942, 2861, 1826, 1694, 1545, 1337, 1269, 1126, 1023. 1H NMR (CDCl3): δ 1.45 (d, 3H); 1.66-1.70 (m, 4H); 2.63-2.66 (m, 2H); 4.09-4.18 (m, 2H); 4.83-4.89 (m, 1H); 5.36 (br d, 1H); 5.45 (m, 1H); 7.16-7.31 (m, 5H).

Provenance & Evidence