Potassium Carbonate → HCID 57672065, compound

HRID 1692103Notes

Reaction equation

HRID 1692103 reaction equation
C(=O)([O-])[O-].[K+].[K+].F[C:8]1[CH:15]=[CH:14][C:11]([C:12]#[N:13])=[CH:10][CH:9]=1.[Cl:16][C:17]1[CH:36]=[C:35]([OH:37])[CH:34]=[C:33]([Cl:38])[C:18]=1[CH2:19][C@@H:20]1[CH2:24][CH2:23][N:22]([N:25]2[CH2:30][CH2:29][CH:28]([OH:31])[CH2:27][CH2:26]2)[C:21]1=[O:32]>CS(C)=O.C(OCC)(=O)C>[Cl:16][C:17]1[CH:36]=[C:35]([CH:34]=[C:33]([Cl:38])[C:18]=1[CH2:19][C@@H:20]1[CH2:24][CH2:23][N:22]([N:25]2[CH2:30][CH2:29][CH:28]([OH:31])[CH2:27][CH2:26]2)[C:21]1=[O:32])[O:37][C:8]1[CH:15]=[CH:14][C:11]([C:12]#[N:13])=[CH:10][CH:9]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 145174-FluorobenzonitrileHCID 57672060HCID 57672060, compound

Product 1

HCID 57672065HCID 57672065, compoundYield 50%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 8857Ethyl AcetateSolvent

Procedure

Add potassium carbonate (0.385 g, 2.8 mmol) and 4-fluorobenzonitrile (0.253 g, 2.1 mmol) to a solution of (R)-3-(2,6-dichloro-4-hydroxy-benzyl)-1-(4-hydroxy-piperidin-1-yl)-pyrrolidin-2-one (0.5 g, 1.4 mmol) in DMSO. Stir the reaction at 80° C. for 3 hours. Cool the reaction, dilute with ethyl acetate, and wash three times with water and one time with brine. After drying the organic layer over sodium sulfate, filter and concentrate under vacuum. Purify the residue by silica gel chromatography with 50% ethyl acetate/hexane to 100% ethyl acetate gradient to afford 0.32 g (50%) of the title compound. MS (m/z): 460 (M+).

Workup

  1. customthe reaction at 80° C. for 3 hours
  2. temperatureCool
  3. customthe reaction
  4. washwash three times with water and one time with brine
  5. dry with materialAfter drying the organic layer over sodium sulfate
  6. filtrationfilter
  7. concentrationconcentrate under vacuum
  8. customPurify the residue by silica gel chromatography with 50% ethyl acetate/hexane to 100% ethyl acetate gradient

Sources & evidence

ORD record
ord-76ceb6626ec74a86a3ae9743c6e7dc09
Source dataset
uspto-grants-2012_04
Patent number
US08153807B2

Reaction notes

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