Vinyl hexanoate → (2R)-2-t-Butoxycarbonylamino-3-n-hexanoyloxy-2-methyl-1-propanol

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Reaction Steps

2-t-Butoxycarbonylamino-2-methylpropane-1,3-diol (20.0 g, 97.4 mmol) was suspended in isopropyl ether (200 mL), and 16.3 mL (0.100 mol) of vinyl hexanoate and lipase [Immobilized lipase from Pseudomonas sp., manufactured by TOYOBO Co., Inc., 0.67 U/mg] (0.8 g) were added thereto, followed by stirring of the mixture at room temperature for 2 hours. After the reaction mixture was filtered, the filtrate was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (hexane:ethyl acetate, 10:1-2:1) to obtain the title compound (25.0 g, yield: 85%).

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