Water → HCID 23138970, compound

HRID 1171640Notes

Reaction equation

HRID 1171640 reaction equation
C([S:4][CH:5]1[CH2:10][CH2:9][N:8]([CH:11]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=2[F:23])[C:12]([CH:14]2[CH2:16][CH2:15]2)=[O:13])[CH2:7]/[C:6]/1=[CH:24]\[C:25]1[O:26][CH:27]=[CH:28][CH:29]=1)(=O)C.C(=O)([O-])[O-].[K+].[K+].O>CO>[CH:14]1([C:12](=[O:13])[CH:11]([N:8]2[CH2:9][CH2:10][CH:5]([SH:4])/[C:6](=[CH:24]/[C:25]3[O:26][CH:27]=[CH:28][CH:29]=3)/[CH2:7]2)[C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=2[F:23])[CH2:16][CH2:15]1

Participants

5

Reactant 3

HCID 962WaterHCID 11430Potassium CarbonateHCID 86609407HCID 86609407, compound

Product 1

HCID 23138970HCID 23138970, compoundYield 45%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of (E)-4-(acetylsulfanyl)-1-[2-cyclopropyl-1-(2-fluorophenyl)-2-oxoethyl]-3-[(furan-2-yl)methylidene]piperidine (100 mg) in methanol (2.5 ml) was added potassium carbonate (50 mg) under ice-cooling, and the resulting mixture was stirred at room temperature for 15 minutes. After stirring, water was added to the reaction mixture, and the resulting mixture was extracted with dichloromethane. The extract was washed with saturated aqueous sodium chloride solution, and the organic layer was dried over anhydrous sodium sulfate. The solvent was removed in vacuo, and the residue was purified using a preparative HPLC [YMC-Pack ODS-A; YMC, mobile phase: a mixture of 70% methanol/water containing acetic acid (0.20%) and triethylamine (0.45%) (70:30, v/v)]. The eluted fraction containing the reaction product was extracted with ethyl acetate, and the organic layer was dried over anhydrous sodium sulfate and evaporated in vacuo to afford the title compound (40 mg, yield: 45%) as pale brown crystals.

Workup

  1. temperaturecooling
  2. stirringAfter stirring
  3. extractionthe resulting mixture was extracted with dichloromethane
  4. washThe extract was washed with saturated aqueous sodium chloride solution
  5. dry with materialthe organic layer was dried over anhydrous sodium sulfate
  6. customThe solvent was removed in vacuo
  7. customthe residue was purified
  8. additionYMC, mobile phase: a mixture of 70% methanol/water
  9. additioncontaining acetic acid (0.20%) and triethylamine (0.45%) (70:30, v/v)]
  10. additionThe eluted fraction containing the reaction product
  11. extractionwas extracted with ethyl acetate
  12. dry with materialthe organic layer was dried over anhydrous sodium sulfate
  13. customevaporated in vacuo

Sources & evidence

ORD record
ord-64de491fef594ffbbc88440e11fbab6a
Source dataset
uspto-grants-2010_11
Patent number
US07829580B2

Reaction notes

Loading…