Sodium Hydroxide → HCID 68429208, compound

Temperature

25 °C

To a solution of the crude 5,5,5-trifluoronorvaline (0.785 g, 4.59 mmol) and NaOH mixture dissolved in THF (10 ml) and 2N NaOH (10 mL) was added dropwise a solution of 5-chlorothiophene-2-sulfonyl chloride (1.32 g, 5.04 mmol) in THF (10 ml) over 30 min. After 60 min, the reaction mixture was allowed to warm gradually to 25° C. and stirred for 16 h. THF was removed in vacuo and the mixture was acidified to a pH of about 2 with 1N HCl. After 15 min, a precipitate began to crash out of the milky white solution. After 60 min, the mixture was cooled to 0° C. for 45 min and then filtered. The precipitate washed with 1N HCl (10 mL) to provide a white solid. The white solid gummed out. It was dissolved in EtOAc (100 mL). The aqueous was washed with EtOAc (3×50 mL) and the organic layers were washed with saturated aqueous NaCl (50 mL). The organic layer was dried over MgSO4, filtered and concentrated to afford N-[(5-chlorothien-2-yl)sulfonyl]-5,5,5-trifluoronorvaline as a dark red oil (1.1 g, 68.3%). Mass Spectrum (−ESI): 350 (M−H).

1. customTHF was removed in vacuo
2. waitAfter 15 min
3. waitAfter 60 min
4. temperaturethe mixture was cooled to 0° C. for 45 min
5. filtrationfiltered
6. washThe precipitate washed with 1N HCl (10 mL)
7. customto provide a white solid
8. washThe aqueous was washed with EtOAc (3×50 mL)
9. washthe organic layers were washed with saturated aqueous NaCl (50 mL)
10. dry with materialThe organic layer was dried over MgSO4
11. filtrationfiltered
12. concentrationconcentrated

ORD record

ord-15d96b9997c14bafb6de6e4f56ae9501

Source dataset

uspto-grants-2009_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07547725B2