反应详情

2-Hydroxy-3-(N-hydroxyamino)propylphosphonic acid (342 mg) was dissolved in a mixture of water (7 ml) and methanol (3 ml). To the solution was added dropwise thienyl acetyl chloride (385 mg) with stirring under ice-cooling, while maintaining the solution at pH 7.2-7.4 with 5% aqueous sodium bicarbonate solution. After the reaction mixture was stirred under ice-cooling for 1.5 hours, the mixture was adjusted to pH 10 with 1 N aqueous sodium hydroxide solution, and stirred under ice-cooling for 2 hours and at ambient temperature for 3 hours. Subsequently, the resultant mixture was adjusted to pH 4.0 with 1N hydrochloric acid, washed with diethyl ether (40 ml) and concentrated under reduced pressure. To the residue was added methanol to give insoluble materials, which was removed by filtration. The filtrate was concentrated under reduced pressure. To the residue was added ethanol (20 ml) and the mixture was stirred at ambient temperature for an hour to give precipitates, which were separated by filtration and dried to give powdery 2-hydroxy-3-(N-hydroxy-N-thienylacetylamino)propylphosphonic acid (0.59 g).

1. temperaturecooling
2. stirringAfter the reaction mixture was stirred under ice-
3. temperaturecooling for 1.5 hours
4. stirringstirred under ice-
5. washwashed with diethyl ether (40 ml)
6. concentrationconcentrated under reduced pressure
7. additionTo the residue was added methanol
8. customto give insoluble materials, which
9. customwas removed by filtration
10. concentrationThe filtrate was concentrated under reduced pressure
11. additionTo the residue was added ethanol (20 ml)
12. stirringthe mixture was stirred at ambient temperature for an hour
13. customto give
14. customprecipitates
15. customwhich were separated by filtration
16. customdried