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

Participants

Reaction Steps

In the same manner as described in Example 2-(5), L-serine benzyl ester (390 mg, 2.0 mmol) was acylated with (R)-3-undecanoyloxytetradecanoic acid (905 mg, 2.2 mmol) in the presence of EDC MeI (745 mg, 2.5 mmol) in CH2Cl2 to afford 1.08 g (92%) of N-[(R)-3-undecanoyloxytetradecanoyl]-L-serine benzyl ester: mp 53–54° C.; 1H NMR (CDCl3) δ 0.88 (t, 6 H, J=6.9 Hz), 1.1–1.7 (m, 44 H), 2.30 (t, 2 H, J=7.7 Hz), 2.49 (d, 2 H, J=5.8 Hz), 3.99 (m, 2 H), 4.65 (m, 1 H), 5.19 (m, 3 H), 6.58 (d, 1 H, J=6.9 Hz), 7.35 (br s, 5 H).

Provenance & Evidence