[C:1]1([CH2:7][CH2:8][CH2:9][C@H:10]([C@H:14]([OH:18])[CH2:15][CH2:16][CH3:17])[C:11]([OH:13])=O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[O:19]1[CH2:24][CH2:23][CH2:22][CH2:21][CH:20]1[O:25][NH2:26].C(Cl)CCl>ClCCl>[O:19]1[CH2:24][CH2:23][CH2:22][CH2:21][CH:20]1[O:25][NH:26][C:11](=[O:13])[C@H:10]([CH2:9][CH2:8][CH2:7][C:1]1[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1)[C@H:14]([OH:18])[CH2:15][CH2:16][CH3:17]To a solution of (2R,3R)-2-(3-phenyl-1-propyl)-3-hydroxyhexanoic acid (1.53 g, 6.12 mmol) in dichloromethane (6 mL) is added 2-tetrahydropyranyloxyamine (0.93 g, 7.96 mmol) and EDC (1.29 g, 6.73 mmol). The resulting solution is stirred at 23° C. for 3 h, concentrated in vacuo, and diluted with 50 mL of EtOAc. The organic layer is washed sequentially with 1 N hydrochloric acid, saturated aqueous sodium bicarbonate solution, saturated aqueous sodium chloride solution, and is dried over anhydrous magnesium sulfate. Concentration under reduced pressure and purification by silica gel chromatography (elution with 2:1 EtOAc-hexanes) provides (2R,3R)-2-(3-phenyl-1-propyl)-3-hydroxyhexanoic acid 2-tetrahydropyranyloxyamide as a solid (1.62 g, 76% yield).
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