Pentanoic Acid → HCID 68809240, compound

Participants

Reaction Conditions

Reaction Steps

Under an atmosphere of nitrogen, to a mixed solution of tetrahydrofuran (383 ml) (hereinafter, abbreviated as THF) and triethylamine (88 ml) was added valeric acid (38 g) and dissolved. To the mixture was dropped pivaloyl chloride (45 ml) at −15° C. to −10° C. The reaction mixture was stirred at −10° C. for 1 hour, and thereto was added anhydrous lithium chloride (12 g). To the mixture was added a solution of (S)-4-isopropyl-2-oxazolidinone (32.3 g) in THF (118 ml), and the reaction mixture was stirred at 25° C. for 15 hours. To the mixture were added an saturated aqueous solution of sodium carbonate and water, and the mixture was stirred for 18 hours. To the reaction mixture were added water, a mixed solvent (n-heptane:ethyl acetate=2:1) (300 ml) and aqueous solution of sodium hydroxide (2 N) (100 ml), and the mixture was extracted. The aqueous layer was extracted with a mixed solvent (n-heptane:ethyl acetate=2:1). The combined organic layer was washed with water, hydrochloric acid (3 N), water, an saturated aqueous solution of sodium bicarbonate, and brine sequentially. The obtained organic layer was dried over anhydrous magnesium sulfate, and filtrated and concentrated to give the title compound (51.5 g) having the following physical data.

Provenance & Evidence