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

Participants

Reaction Steps

To a suspension of 2-t-butoxycarbonylamino-2-ethylpropane-1,3-diol (52.9 g, 241 mmol) in isopropyl ether (1.0 l) were added successively vinyl hexanoate (41 ml, 254 mmol) and lipase [Immobilized lipase from Pseudomonas sp., TOYOBO, 0.67 U/mg] (2.1 g) with stirring, and the resulting mixture was stirred at room temperature for 4 hours. After stirring, the reaction mixture was filtered and evaporated in vacuo, and the residue was purified by chromatography on a silica gel column using a mixed solvent of hexane and ethyl acetate (7:1-4:1-2:1) as the eluent to afford the title compound (66.8 g, yield: 87%).

Provenance & Evidence