(S)-Benzyl 2-amino-3-hydroxypropanoate → N-[(R)-3-octanoyloxytetradecanoyl]-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-octanoyloxytetradecanoic acid (815 mg, 2.2 mmol) in the presence of EDC·MeI (745 mg, 2.5 mmol) in CH2Cl2 to afford 1.02 g (93%) of N-[(R)-3-octanoyloxytetradecanoyl]-L-serine benzyl ester: mp 50-51° C.; 1H NMR (CDCl3) δ 0.88 (t, 6H, J=6.8 Hz), 1.1-1.7 (m, 30H), 2.30 (t, 2 H, J=7.7 Hz), 2.51 (d, 2H, J=5.8 Hz), 2.60 (t, 1H, J=6.0 Hz), 3.97 (m, 2H), 4.65 (m, 1H), 5.22 (m, 3H), 6.61 (d, 1H, J=6.9 Hz), 7.35 (br s, 5H).

Provenance & Evidence