(R)-3-tetradecanoyloxytetradecanoic acid → N-(2-hydroxyethyl)-N-[(R)-3-tetradecanoyloxytetradecanoyl]glycine t-butyl ester

Participants

Reaction Steps

In the same manner as described in Example 2-(5), N-(2-hydroxyethyl)glycine t-butyl ester (0.25 g, 1.43 mmol) was acylated with (R)-3-tetradecanoyloxytetradecanoic acid (0.714 g, 1.57 mmol) in the presence of EDC·MeI (0.466 g, 1.57 mmol) to give 0.46 g (51%) of N-(2-hydroxyethyl)-N-[(R)-3-tetradecanoyloxytetradecanoyl]glycine t-butyl ester as an amorphous solid: 1H NMR (CDCl3) δ 0.88 (t, 6H, J=6.5 Hz), 1.15-1.7 (m, 51H), 2.26 (t, 2H, J=7.5 Hz), 2.60 (dd, 1H, J=6.5, 15 Hz), 2.86 (dd, 1H, J=6.7, 15 Hz), 3.40-4.15 (m, 7H), 5.25 (m, 1H).

Provenance & Evidence