Triethylamine → HCID 73291822, compound

Participants

Reaction Conditions

Reaction Steps

In a four-necked round bottom flask, Et3N (1.5 mL, 10.9 mmol) was added to a solution of (2R,3S)-3-hydroxy-2-{[(octyloxy)carbonyl]amino}butanoic acid (1 g, 3.63 mmol) in dry CH2Cl2 (40 mL) under argon. After cooling at 0° C., HBTU (2.07 g, 5.45 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 column chromatography, eluting with Cy/AcOEt (from 95:5 to 60:40). The resulting white solid (ca. 0.19 g) was further triturated with cyclohexane, to afford a pure compound (0.165 g, 18%) as white solid. MS (ESI) m/z: 256.31 [M−H]−. FTIR (cm−1): 3326, 2958, 2924, 2856, 1857, 1692, 1547, 1333, 1270, 1087, 1025, 845. 1H NMR (CDCl3): δ 0.87-0.90 (t, 3H); 1.28-1.36 (m, 10H); 1.47 (t, 3H); 1.59-1.66 (m, 2H); 4.06-4.15 (m, 2H); 4.84-4.91 (m, 1H); 5.38-5.48 (m, 2H).

Provenance & Evidence