Hydrochloric Acid → 3-(Butylamino)propane-1,1-bisphosphonic acid

Temperature

0 °C

A solution of N-butyl-3,3-bis(diethoxyphosphinyl)propionamide (1.40 g, 3.5 mmol) in THF (9 mL) was cooled to 0° C., and borane-methyl sulfide (0.90 ml, 9.0 mmol) was added via syringe. The reaction was stirred at 0° C. for 5 minutes, then warmed to 65° C. for 3 hours. The reaction mixture was cooled to 0° C. and 6N HCl (6 ml) was added carefully. The solvent was removed in vacuo, and the residue was repeatedly concentrated from methanol (3×10 mL). The product was dissolved in 12N HCl and heated at reflux for 20 hours. After cooling, the volatile materials were removed under vacuum, the residue was dissolved in water (10 mL) and then concentrated to give 1.05 g of Compound No. 158 as a hygroscopic glass.

1. temperaturewarmed to 65° C. for 3 hours
2. temperatureThe reaction mixture was cooled to 0° C.
3. customThe solvent was removed in vacuo
4. concentrationthe residue was repeatedly concentrated from methanol (3×10 mL)
5. dissolutionThe product was dissolved in 12N HCl
6. temperatureheated
7. temperatureat reflux for 20 hours
8. temperatureAfter cooling
9. customthe volatile materials were removed under vacuum
10. dissolutionthe residue was dissolved in water (10 mL)
11. concentrationconcentrated

ORD record

ord-3f7c12ece3d5427682be4ea183c9152d

Source dataset

uspto-grants-1998_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05728650