Benzyl chloroformate → HCID 69462213, compound

Participants

Reaction Steps

(Ozinskas et al., J. Org. Chem. 1986. 51: 4057-5050). To a suspension of starting material 31 (Cosmoferm B. V., Delft, Netherlands) (6.35 g, 20 mmol) in aqueous NaHCO3 (1 N, 80 ml, 4 equiv.) and 1,4-dioxane (30 ml) was added benzyl chloroformate (3.31 ml, 1.1 equiv.). The reaction mixture was stirred at rt overnight, whereupon t.l.c (only ethyl acetate or DCM-MeOH 5:1) indicated the reaction was finished. The suspension was diluted with EtOAc and poured onto water. After separation, the aqueous phase was extracted with EtOAc (3×). The combined organic solutions were washed aqueous NH4Cl, brine, dried over Na2SO4, and concentrated to afford a residue. The residue was purified by flash column chromatography (Petroether-EtOAc, 2:1 to only EtOAc) to provide compound 32 (8.13 g, 90%) as a white solid.

Provenance & Evidence