Potassium Carbonate → HCID 84708577, compound

HRID 1841975Notes

Reaction equation

HRID 1841975 reaction equation
[C:1]([O:5][C:6](=[O:23])[NH:7][C:8]1[S:9][C:10]2[CH2:11][N:12](C(=O)C(F)(F)F)[CH2:13][CH2:14][C:15]=2[N:16]=1)([CH3:4])([CH3:3])[CH3:2].C(=O)([O-])[O-].[K+].[K+]>CO.O>[C:1]([O:5][C:6](=[O:23])[NH:7][C:8]1[S:9][C:10]2[CH2:11][NH:12][CH2:13][CH2:14][C:15]=2[N:16]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 2

HCID 11430Potassium CarbonateHCID 86695355HCID 86695355, compound

Product 1

HCID 84708577HCID 84708577, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Conditions

Temperature
25 °C

Procedure

To a suspension of [5-(2,2,2-trifluoro-acetyl)-4,5,6,7-tetrahydro-thiazolo[5,4-c]pyridin-2-yl]-carbamic acid tert-butyl ester (3.50 g, 9.86 mmol) in MeOH (75 mL) is added a solution of potassium carbonate (13.8 g; 98.6 mmol) in water (125 mL) and the reaction stirred at about 25° C. for 24 hours. The suspension is concentrated and the residue suspended in EtOAc (300 mL). This is washed with sat. NH4Cl (300 mL) then brine (100 mL). Solid product forms in the EtOAc layer. This is filtered off as crop 1. The aqueous layer is extracted with more EtOAc (3×300 mL) and the combined extracts washed with brine and dried (Na2SO4). Concentrate to a white solid and combine with the above precipitate. Triturate this in EtOAc (50 mL) and filter to give the title compound (N).

Workup

  1. concentrationThe suspension is concentrated
  2. washThis is washed with sat. NH4Cl (300 mL)
  3. filtrationThis is filtered off as crop 1
  4. extractionThe aqueous layer is extracted with more EtOAc (3×300 mL)
  5. washthe combined extracts washed with brine
  6. dry with materialdried (Na2SO4)
  7. concentrationConcentrate to a white solid
  8. customTriturate this in EtOAc (50 mL)
  9. filtrationfilter

Sources & evidence

ORD record
ord-be0e9668e7f14a59bd8bbac618a83256
Source dataset
uspto-grants-2015_02
Patent number
US08946203B2

Reaction notes

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