Water → HCID 59571717, compound

Participants

Reaction Conditions

Reaction Steps

9.1 mL of 2.44M n-butyllithium tetrahydrofuran solution was added thereto dropwise to tetrahydrofuran (30 mL) solution of 3.92 g of (S)-4-benzyl-2-oxazolidinone at −50° C. The mixture was stirred at −50° C. for 1 hour. Thereafter, the solution of the previously prepared (±)-{9-[3-methoxy-4-(5-methyl-2-phenyl-oxazole-4-ylmethoxy)-benzyl]-9H-carbazole-4-yloxy}phenylacetyl chloride in tetrahydrofuran (30 mL) was added thereto dropwise at −50° C. After the dropwise addition thereto, the mixture was stirred at room temperature overnight. Water was added to the reaction mixture, and extracted with ethyl acetate. The extract was washed with brine, and dried over anhydrous sodium sulfate. After filtration, the filtrate was concentrated in vacuo, the prepared diastereomer mixture was purified by medium-pressure silica gel chromatography (ethyl acetate:n-hexane=5:1), and two types of the subject compound, 1.52 g of compound A (first fraction) and 1.2 g compound B (second fraction), were respectively prepared as pale brown powder.

Provenance & Evidence