Acetone → HCID 178471739, compound

HRID 1623569Notes

Reaction equation

HRID 1623569 reaction equation
[C:1]([O-:4])([O-])=[O:2].[K+].[K+].C(O[C:10](=O)[CH2:11][C:12]([NH:14][C:15]([NH:17][C:18]1[CH:23]=[CH:22][C:21]([F:24])=[C:20]([C:25]([F:28])([F:27])[F:26])[CH:19]=1)=[S:16])=[O:13])C.[CH3:30]I.[CH3:32][C:33](C)=O>>[CH2:32]([O:4][C:1](=[O:2])[CH:11]([CH3:10])[C:12](/[N:14]=[C:15](/[NH:17][C:18]1[CH:23]=[CH:22][C:21]([F:24])=[C:20]([C:25]([F:26])([F:27])[F:28])[CH:19]=1)\[S:16][CH3:30])=[O:13])[CH3:33]

Participants

5

Reactant 4

HCID 180AcetoneHCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 59627506HCID 59627506, compound

Product 1

HCID 178471739HCID 178471739, compound

Procedure

K2CO3 (0.831 g; 6.01 mmol) was added to a stirred solution of intermediate D15 (1.765 g; 5.01 mmol) in acetone (50 ml) at room temperature. After 40 minutes, CH3I (0.624 ml; 10.0 mmol) was added dropwise. The reaction mixture was stirred at room temperature. The solvent was removed under reduced pressure and the residue partitioned between H2O/DCM. The aqueous phase was extracted with DCM and the combined organic extracts were washed with brine, dried (Na2SO4) and filtered yielding an orange oil. LCMS showed 4 different products which were separated by flash chromatography using the Biotage system (40M column), eluent: DCM to 10% MeOH/DCM gradient elution. The third fraction contained the desired compound. Yield: 401 mg of intermediate D16.

Workup

  1. customThe solvent was removed under reduced pressure
  2. customthe residue partitioned between H2O/DCM
  3. extractionThe aqueous phase was extracted with DCM
  4. washthe combined organic extracts were washed with brine
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. customyielding an orange oil
  8. customwere separated by flash chromatography
  9. washDCM to 10% MeOH/DCM gradient elution

Sources & evidence

ORD record
ord-77e7c2d60e5948508cdc31513479f1e5
Source dataset
uspto-grants-2014_07
Patent number
US08778974B2

Reaction notes

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