Sodium Bicarbonate → HCID 86728108, compound

HRID 627639Notes

Reaction equation

HRID 627639 reaction equation
[NH2:1][C:2]1[C:7]([CH3:9])([CH3:8])[S:6](=[O:11])(=[O:10])[CH2:5][C@:4]([C:14]2[CH:19]=[C:18](Br)[CH:17]=[CH:16][C:15]=2[F:21])([CH2:12][F:13])[N:3]=1.C(=O)(O)[O-].[Na+]>C(O)C.C(OCC)(=O)C.[Pd]>[NH2:1][C:2]1[C:7]([CH3:9])([CH3:8])[S:6](=[O:11])(=[O:10])[CH2:5][C@@:4]([CH2:12][F:13])([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=2[F:21])[N:3]=1

Participants

6

Reactant 2

HCID 516892Sodium BicarbonateHCID 86715851HCID 86715851, compound

Product 1

HCID 86728108HCID 86728108, compoundYield 97.5%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of (S)-5-amino-3-(5-bromo-2-fluorophenyl)-3-(fluoromethyl)-6,6-dimethyl-3,6-dihydro-2H-1,4-thiazine 1,1-dioxide (3.22 g, 8.44 mmol) in ethanol (15 mL) and ethyl acetate (5 mL) was added sodium bicarbonate (138 mg, 1.69 mmol) and 10 wt % palladium on carbon (0.90 g, 8.44 mmol). The flask was evacuated and backfilled with hydrogen three times, and stirred at room temperature under a hydrogen atmosphere for 2 hours. The reaction mixture was filtered through a Celite pad, and the filter cake was rinsed with ethyl acetate and ethanol. The combined filtrates were concentrated in vacuo and the residue was redissolved in ethyl acetate, washed with saturated aqueous sodium bicarbonate, dried over sodium sulfate, filtered and evaporated to provide the title compound (2.49 g, 8.23 mmol) as an off-white solid. LC/MS (ESI+) m/z=303 (M+H).

Workup

  1. customThe flask was evacuated
  2. filtrationThe reaction mixture was filtered through a Celite pad
  3. washthe filter cake was rinsed with ethyl acetate and ethanol
  4. concentrationThe combined filtrates were concentrated in vacuo
  5. dissolutionthe residue was redissolved in ethyl acetate
  6. washwashed with saturated aqueous sodium bicarbonate
  7. dry with materialdried over sodium sulfate
  8. filtrationfiltered
  9. customevaporated

Sources & evidence

ORD record
ord-c6dbb4a272cd4373988ecd5817a35f82
Source dataset
uspto-grants-2016_04
Patent number
US09309263B2

Reaction notes

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