(R)-3-tetradecanoyloxytetradecanoic acid → 3-benzyloxy-(R)-2-[(R)-3-tetradecanoyloxytetradecanoylamino]propanol

Participants

Reaction Steps

A solution of (R)-2-amino-3-benzyloxy-1-propanol (0.46 g, 2.33 mmol) and (R)-3-tetradecanoyloxytetradecanoic acid (1.29 g, 2.83 mmol) in CH2Cl2 (20 mL) was treated with EDC·MeI (0.78 g, 2.79 mmol) and stirred for 16 h at room temperature. The reaction mixture was filtered through a short pad of Celite® and concentrated. Flash chromatography on silica gel with 45% EtOAc-hexanes afforded 1.1 g (69%) of 3-benzyloxy-(R)-2-[(R)-3-tetradecanoyloxytetradecanoylamino]propanol as a colorless solid: mp 42-44.5° C.; 1H NMR δ 0.88 (t, 6H, J=6.5 Hz), 1.0-1.7 (m, 42 H), 2.50 (t, 2H, J=7.5 Hz), 2.46 (m, 2H), 3.56 (br s, 1H), 3.5-3.75 (m, 3H), 3.78 (dd, 1H, J=11, 4 Hz), 4.08 (m, 1H), 4.51 (s, 2H), 5.17 (m, 1H), 6.36 (d, 1H, J=7.8 Hz), 7.2-7.4 (m, 5H).

Provenance & Evidence