Acetone → HCID 86660265, compound

Participants

Reaction Steps

(S)-6-(4-Amino-benzoylamino)-2-carbazol-9-yl-hexanoic acid methyl ester 12 (0.220 g, 0.513 mmol) was dissolved in 5% HCl (9.0 mL) and acetone (9.0 mL) at 0° C. in the dark. NaNO2 (0.039 g, 0.564 mmol) in 2.0 mL H2O was added to the reaction mixture, causing a color change to pale yellow. After 30 min of stiffing, NaN3 (0.333 g, 5.13 mmol) in 5.0 mL H2O was added to the reaction mixture at 0° C. causing an immediate color change from yellow to colorless. The reaction mixture was further stirred for additional 15 min, poured into water (10 mL), and extracted with ethyl acetate (30 mL×2). The combined organic extract was washed with water (10 mL×2) and brine (10 mL×2), dried over anhydrous Na2SO4 and evaporated under reduced pressure. The crude residue was purified by flash column chromatography on silica gel (230-400 mesh), eluting with hexane:acetone (90:10 to 80:20) to furnish a yellow solid (S) 6-(4-azido-benzoylamino)-2-carbazol-9-yl-hexanoic acid methyl ester 13 (0.200 g, 86%).

Provenance & Evidence