Triethylamine → N-[(R)-3-tetradecanoyloxytetradecanoyl]-L-serinamide

Participants

Reaction Steps

A suspension of L-serinamide hydrochloride (0.157 g, 1.18 mmol) and (R)-3-tetradecanoyloxytetradecanoic acid (0.61 g, 1.34 mmol) in CH2Cl2 (6 mL) was treated with triethylamine (0.18 mL, 1.3 mmol) and the resulting solution was stirred with 4 Å molecular sieves for 30 min. EEDQ (0.437 g, 1.77 mmol) was then added and the mixture was stirred for 16 h at room temperature. The product that precipitated was collected and washed with CH2Cl2 (2×25 mL) to give 0.455 g (71%) of N-[(R)-3-tetradecanoyloxytetradecanoyl]-L -serinamide as a colorless powder: mp 126-130° C.; 1H NMR (CDCl3) δ 0.88 (t, 6H, J=˜7 Hz), 1.15-1.7 (m, 42 H), 2.31 (t, 2 H, J=7.5 Hz), 2.51 (d, 2 H, J=6.3 Hz), 3.56 (br s, 1 H), 3.65 (dd, 1 H, J=1 1.2, 5.5 Hz), 3.86 (dd, 1 H, J=1 1.2, 4.5 Hz), 4.21 (s, 2 H), 4.40 (m, 1 H), 5.22 (m, 1 H).

Provenance & Evidence