18-Crown-6 → HCID 131714464, compound

Participants

Reaction Steps

Potassium fluoride (117 mg, 2.02 mmole) was added to 10 ml of dry acetonitrile containing 1,4,7,10,13,16-hexaoxacyclooctadecane (266 mg, 1.01 mmole). To this solution were added 7-[(1H-indol-3-yl)methyl]quinazolino-(3,2-A)-1,4-benzodiazepin-5,13-(6H,7H)-dione (492 mg, 1.01 mmole), p-nitrophenyl-2(S)-((1,1-dimethyl)ethoxycarbonyl)amino-4-methylpentanoate (441 mg, 1.25 mmole) and 218 μl (1.25 mmole) of diisopropylethylamine under nitrogen. The reaction mixture was stirred rapidly, 10 ml of dimethylformamide was added, and one equivalent of each of the above reagents was added. After 60 hours, the reaction mixture was partitioned between ethyl acetate and water; the phases were separated and the organic layer was washed in succession with saturated sodium bicarbonate solution, 10% citric acid solution, and brine. Rotoevaporation of the dried (MgSO4) extracts gave a solid which was purified by silica gel chromatography (1:1 hexaneethyl acetate v/v).

Provenance & Evidence