(S)-Benzyl 2-amino-3-hydroxypropanoate → N-[(R)-3-tetradecanoyloxytetradecanoyl]-L-serine benzyl ester

Participants

Reaction Steps

In the same manner as described in Example 2-(5), L-serine benzyl ester (0.212 g, 1.08 mmol) was acylated with (R)-3-tetradecanoyloxytetradecanoic acid (0.541 g, 1.19 mmol) in the presence of EDC-MeI (0.353 g, 1.19 mmol) to give 0.642 g (94%) of N-[(R)-3-tetradecanoyloxytetradecanoyl]-L-serine benzyl ester as a waxy solid: mp 56-61° C.; 1H NMR (CDCl3) δ 0.88 (t, 6 H, J=7 Hz), 1.1-1.7 (m, 42 H), 2.29 (t, 2 H, J=7.5 Hz), 2.50 (m, 2 H), 3.87 (br t, 1 H), 3.95 (m, 2 H), 4.65 (m, 1 H), 5.1-5.25 (m, 3 H), 6.69 (d, 1 H, J=7 Hz), 7.34 (br s, 5 H).

Provenance & Evidence