Epichlorohydrin → HCID 54456275, compound

Participants

Reaction Conditions

Reaction Steps

N-(N-(N-(N-(4-(Oxlranylmethoxy)benzoyl)glycyl) phenylalanyl) leucyl) glycine N-(2-(4-(oxiranylmethoxy)phenyl)ethyl)amide. N-(N-(N-(N-(4-Hydroxybenzoyl)-glycyl)phenylalanyl)leucyl)glycine N-(2-(4-hydroxyphenyl) ethyl)amide (106 mg, 0.131 mol) was suspended in water (12 mL) containing sodium hydroxide (52.3 mg, 1.31 mmol). Chloromethyloxirane (604 mg, 6.5 mmol) in methanol (10 mL) was added, followed by phenylmethyltrimethylammonium hydroxide (40% aqueous solution, 90 mg). The solution was stirred for 48 h at 40° C. The solvent and excess reagent were evaporated under reduced pressure. The residue was dissolved in ethyl acetate and was washed with water. The solution was dried with anhydrous magnesium sulphate. The solvent was evaporated under reduced pressure. Column chromatography (silica gel; ethyl acetate, then ethyl acetate/methanol 39:1, then ethyl acetate/methanol 19:1, then ethyl acetate/methanol 9:1) gave N-(N-(N-(N-(4-(oxiranylmethoxy)benzoyl)glycyl)phenylalanyl)leucyl)glycine N-(2-(4-(oxiranyl-methoxy)phenyl)ethyl)amide (26.5 mg, 27%).

Provenance & Evidence