Reaction Steps
Add glycine methyl ester hydrochloride (95 mg, 0.755 mmol), HOBT (102 mg, 0.755 mmol), EDCI (206 mg, 1.08 mmol), and Et3N (0.4 ml, 0.726 mmol) to diastereomeric isomer pair 1 of 6-{1-ethyl-1-[4-(1-ethyl-2-hydroxy-3,3-dimethyl-butoxy)-3-methyl-phenyl]-propyl}-naphthalene-2-carboxylic acid (343 mg, 0.72 mmol) and CH2Cl2 (5 ml). Stir the reaction for 14 h. Concentrate the reaction mixture in vacuo, and chromatograph the residue (CH2Cl2 to 15% EtOAc/CH2Cl2) to give the title compound as a colorless foam (373 mg, 95%). 1NMR (400 MHz, CDCl3) δ ppm: 0.64 (t, J=7.6 Hz, 6H), 0.93 (t, J=8.4 Hz, 3H), 0.93 (s, 9H), 1.68 (m, 1H), 1.81 (m, 1H), 2.12 (s, 3H), 2.18 (q, 4H), 2.60 (bs, 1H), 3.27 (s, 1H), 3.83 (s, 3H), 4.27 (dd, J=5.6, 3.2 Hz, 1H), 4.31 (d, J=5.2 Hz, 2H), 6.63 (d, J=8.0 Hz, 1H), 6.75 (t, J=4.8 Hz, 1H), 6.89 (d, J=2.4 Hz, 1H), 6.93 (dd, J=6.4, 2.0 Hz, 1H), 7.18 (dd, J=6.8, 2.0 Hz, 1H), 7.75 (d, J=8.4 Hz, 1H), 7.83 (d, J=2.0, 1H), 7.86 (m, 2H), 8.26 (s, 1H). High Res. ES-MS: 570.3116; calc. for C34H45NO5+Na: 570.3196.
