Methanol → HCID 131719493, compound

Participants

Reaction Steps

Borane dimethylsulfide complex (10 molar, 0.9 ml., 9 mmole) was added dropwise to a tetrahydrofuran solution (3 ml.) of [1S-(1R*,2S*,3S*)]-N-[4-[(butylamino)sulfonyl]-1-(cyclohexylmethyl)-2,3-dihydroxybutyl]-4-methylpentanamide (100 mg., 0.23 mmole, product of Example 38). The reaction mixture is stirred at 50° for one hour, quenched with 1N HCl (10 ml.), and after 30 minutes, saturated sodium bicarbonate was added (pH 8). The product was extracted with ethyl acetate (2×150 ml.) and this solution was washed with brine, dried (Na2SO4), filtered, and concentrated in vacuo. The resulting crude product was purified by chromatography through silica gel (20 g., Merck) using (2.5:0.1:100) methanol:acetic acid:chloroform. The appropriate fractions were combined and concentrated to yield 63 mg. of glassy, very hygroscopic white solid [βR-(βR*,γR*,δS*)]-N-butyl-β, γ-dihydroxy-δ-[(4-methylpentyl)amino]cyclohexanepentanesulfonamide, monoacetate salt; m.p. 68°-82°, [α]D =+14° (c=0 5, methanol). TLC (silica gel, methanol:chloroform, 1:9) Rf =0.46.

Provenance & Evidence