Methanol → HCID 59398348, compound

HRID 2193053Notes

Reaction equation

HRID 2193053 reaction equation
CO.[C:3]([O:7][C:8](=[O:30])[N:9]([CH2:22][CH2:23][S:24][C:25]1[S:26][CH:27]=[CH:28][CH:29]=1)[CH:10]1[CH2:15][CH2:14][N:13](C(=O)C(F)(F)F)[CH2:12][CH2:11]1)([CH3:6])([CH3:5])[CH3:4].C(=O)([O-])[O-].[K+].[K+]>O.C(OCC)(=O)C.O1CCCC1>[C:3]([O:7][C:8](=[O:30])[N:9]([CH:10]1[CH2:11][CH2:12][NH:13][CH2:14][CH2:15]1)[CH2:22][CH2:23][S:24][C:25]1[S:26][CH:27]=[CH:28][CH:29]=1)([CH3:6])([CH3:4])[CH3:5]

Participants

7

Reactant 3

HCID 887Methanol2×HCID 11430Potassium CarbonateHCID 59397998HCID 59397998, compound

Product 1

HCID 59398348HCID 59398348, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To 1 mL of a methanol solution containing 66 mg of tert-butyl(2-(2-thienylthio)ethyl)(1-(trifluoroacetyl) piperidin-4-yl)carbamate, 0.2 mL of water was added, and 32 mg of potassium carbonate was added under cooling with ice, and the mixture was stirred at a room temperature for 20 minutes. Thereto was added 0.5 mL of methanol, and the mixture was stirred at room temperature for 1 hour and 10 minutes. The reaction mixture was added with 0.6 mL of tetrahydrofuran, and stirred for 10 minutes, and the solvent was removed under reduced pressure. The residue thus obtained was added with ethyl acetate and water. The organic layer was separated, washed with an aqueous saturated sodium chloride solution and dried over anhydrous magnesium sulfate, and the solvent was removed under reduced pressure to obtain 43 mg of a colorless oily substance, tert-butyl(piperidin-4-yl)(2-(2-thienylthio)ethyl)carbamate.

Workup

  1. additionwas added
  2. temperatureunder cooling with ice
  3. stirringthe mixture was stirred at room temperature for 1 hour and 10 minutes
  4. stirringstirred for 10 minutes
  5. customthe solvent was removed under reduced pressure
  6. customThe residue thus obtained
  7. customThe organic layer was separated
  8. washwashed with an aqueous saturated sodium chloride solution
  9. dry with materialdried over anhydrous magnesium sulfate
  10. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-581f7b5dfc2b42499784582d1fc7cb7e
Source dataset
uspto-grants-2012_12
Patent number
US08329694B2

Reaction notes

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