Dimethylformamide → Digoxin

Participants

Reaction Steps

To 25 mg (0.05 mmol) of DCAS bis-hydrazide prepared as described in Example 6 and 78 mg (0.10 mmol) of digoxin dialdehyde prepared as above was added 2 ml of dry dimethylformamide and 17 μl (0.10 mmol) of N,N-diisopropylethylamine. The reaction was stirred at room temperature under nitrogen for 48 hours, during which time a new product formed. By thin layer chromatography, using chloroform-methanol (9:1, v/v) as developing solvent; this product had Rf 0.45 and was blue-green in color. The reaction mixture was evaporated to dryness by rotary evaporation and purified by preparative thin layer chromatography on two 20×20 cm silica gel type GF preparative plates, using chloroform-methanol (9:1, v/v) as developing solvent. The band corresponding to the produce at Rf 0.45 was scraped off the plate and eluted from the silica gel with methanol. Evaporation of methanol yielded a dark greenish-blue solid product.

Provenance & Evidence