Hydrochloric Acid → HCID 67479046, compound

197 f) To a solution of 2-[2-(methanesulfonyl-methyl-amino)-phenyl]-propionic acid (0.755 g, 2.93 mmol) and diphenylphosphonic azide (0.95 mL, 4.4 mmol) in dichloromethane (25 mL) was added triethylamine (0.65 mL, 4.7 mmol). The mixture was stirred at room temperature for 24 hours then cooled to 5° C. and 2N Hydrochloric acid (30 mL) was added and the mixture stirred for 10 minutes. The layers were separated and the aqueous was washed with dichloromethane (2×10 mL). The combined organic layers were dried over magnesium sulfate, filtered and evaporated. The residue dissolved in tert-butyl alcohol (10 mL, 100 mmol) and heated at 80° C. for 18 hours. The volatiles were evaporated and the residue was dissolved in ethyl acetate (50 mL). The organic layer was washed with saturated aqueous sodium carbonate (30 mL), dried over magnesium sulfate, filtered and evaporated. The residue was dissolved in dichloromethane (5 mL) and trifluoroacetic acid (2 mL, 20 mmol) was added. The mixture was stirred at room temperature overnight. The volatiles were evaporated. The residue was dissolved in ethyl acetate (50 mL) and was extracted with 2N Hydrochloric acid (3×20 mL). The combined acidic aqueous layers were basified with 2M sodium hydroxide to pH 10. The basic aqueous layer was extracted with dichloromethane (3×20 mL). The combined organic layers were dried over magnesium sulfate, filtered and evaporated. N-[2-(1-Amino-ethyl)-phenyl]-N-methyl-methanesulfonamide was isolated as a crude tan viscous oil (0.380 g, 56%).

1. temperaturethen cooled to 5° C.
2. stirringthe mixture stirred for 10 minutes
3. customThe layers were separated
4. washthe aqueous was washed with dichloromethane (2×10 mL)
5. dry with materialThe combined organic layers were dried over magnesium sulfate
6. filtrationfiltered
7. customevaporated
8. temperatureheated at 80° C. for 18 hours
9. customThe volatiles were evaporated
10. dissolutionthe residue was dissolved in ethyl acetate (50 mL)
11. washThe organic layer was washed with saturated aqueous sodium carbonate (30 mL)
12. dry with materialdried over magnesium sulfate
13. filtrationfiltered
14. customevaporated
15. dissolutionThe residue was dissolved in dichloromethane (5 mL)
16. stirringThe mixture was stirred at room temperature overnight
17. customThe volatiles were evaporated
18. dissolutionThe residue was dissolved in ethyl acetate (50 mL)
19. extractionwas extracted with 2N Hydrochloric acid (3×20 mL)
20. extractionThe basic aqueous layer was extracted with dichloromethane (3×20 mL)
21. dry with materialThe combined organic layers were dried over magnesium sulfate
22. filtrationfiltered
23. customevaporated

ORD record

ord-0ff30858ae2a48d880a3745403186171

Source dataset

uspto-grants-2014_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08633173B2