Phenylacetylene → HCID 12173661, compound

Participants

Reaction Conditions

Reaction Steps

A solution of copper (II) acetate monohydrate (10.0 mg, 0.050 mmol) in water (0.2 ml) was treated with sodium (L)-ascorbate (20 mg, 0.10 mmol), the mixture was stirred until the mixture was turned bright orange (3 min). Subsequently, (R,M)-3-{[4-(2-diphenylphosphanyl-7-methoxy-naphthalen-1-yl)-phthalazin-1-ylaminol]-phenyl-methyl}-pentan-3-ol (1st diastereomer, 33.1 mg, 0.050 mmol) and phenylacetylene (0.275 ml, 2.5 mmol) were added, the resulting mixture was stirred for 10 min at 23° C., cooled to 0° C., stirred for 5 min and treated with 5-(1-isopentylidene)-2,2-dimethyl-1,3-dioxane-4,6-dione (53 mg, 0.25 mmol). The reaction mixture was stirred vigorously at 0° C. for 24 hrs, diluted with dichloromethane (2 ml) and subjected directly to flash chromatography on silica gel (hexane/EtOAc 5:1) to give 67 mg of the pure title compound as a white solid. (Yield: 85%)

Provenance & Evidence