Ethanol → HCID 22811228, compound

Participants

Reaction Steps

Diethyl 3-(N-ethoxycarbonyl-N-ethoxycarbonyloxyamino)-2(R)-hydroxypropylphosphonate (13.8 g) was dissolved in dichloromethane (25 ml). To the solution was added trimethylbromosilane (25 g) under ice-cooling. The reaction mixture was stirred at the same temperature for 30 minutes and at ambient temperature for 1.5 hours. Subsequently, the resultant mixture was concentrated under reduced pressure to give a residue, which is dissolved in water (50 ml). The aqueous solution was stirred at ambient temperature for an hour, washed three times with chloroform (20 ml) and then the aqueous layer was separated. After 1 N hydrochloric acid (140 ml) was added to the aqueous layer, the mixture was heated to reflux for 15 hours. The resultant mixture was concentrated under reduced pressure to give a residue, which was dissolved in a mixture of water (10 ml) and methanol (20 ml). The solution was adjusted to pH 3-4 with propyleneoxide (20 ml) and ethanol (200 ml) was added to the solution to precipitate an oil, which was separated by decantation, washed with ethanol (20 ml) and dissolved in water (20 ml). After the aqueous solution was treated with activated charcoal (100 ml), the activated charcoal was removed by filtration. The filtrate was evaporated to dryness under reduced pressure and dried over phosphorus pentoxide to give powdery 2(R)-hydroxy-3-(N-hydroxyamino)propylphosphonic acid (1.15 g).

Provenance & Evidence