hydroxylamine-O-sulfonic acid → 2-(5-Bromothiazol-2-yl)propane-2-sulfonamide

The product of Step 4 (2.50 g, 7.02 mmol) was taken up in THF (80 mL) at room temperature, and NaOMe (25% in MeOH, 1.52 g, 7.02 mmol) was added. After 30 min at room temperature, the suspension was evaporated to dryness, providing a white solid. The solid was taken up in water (50 mL), and a solution of NaOAc (3.17 g, 38.6 mmol) and hydroxylamine-O-sulfonic acid (3.97 g, 35.1 mmol) in water (25 mL) was added while cooling the reaction (0° C.). The reaction was vigorously stirred at room temperature overnight (a white solid precipitated after 15-30 min). The reaction was extracted with ethyl acetate (2×). The combined organic layers were washed with brine, dried (MgSO4), filtered and evaporated. The resulting white residue was triturated with CH2Cl2 and filtered to provide 2-(5-bromo-1,3-thiazol-2-yl)propane-2-sulfonamide (1.58 g, 79%) as a white powder. ESI: [M+H]+ m/z 284.9/286.9.

1. customthe suspension was evaporated to dryness
2. customproviding a white solid
3. temperaturewhile cooling
4. customthe reaction (0° C.)
5. customprecipitated after 15-30 min)
6. extractionThe reaction was extracted with ethyl acetate (2×)
7. washThe combined organic layers were washed with brine
8. dry with materialdried (MgSO4)
9. filtrationfiltered
10. customevaporated
11. customThe resulting white residue was triturated with CH2Cl2
12. filtrationfiltered

ORD record

ord-67a6793501964f9fa503e20d93e62d94

Source dataset

uspto-grants-2014_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08759366B2