Potassium Carbonate → (2S,3R)-2-[2-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)ethyl]-3-hydroxy-5-[4-(trifluoromethyl)phenyl]pentanoic acid

HRID 2410433Notes

Reaction equation

HRID 2410433 reaction equation
C(=O)([O-])[O-].[K+].[K+].[O:7]=[C:8]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[C:10](=[O:17])[N:9]1[CH2:18][CH2:19][C@@H:20]([C@H:24]([O:37]C=O)[CH2:25][CH2:26][C:27]1[CH:32]=[CH:31][C:30]([C:33]([F:36])([F:35])[F:34])=[CH:29][CH:28]=1)[C:21]([OH:23])=[O:22]>CO>[O:7]=[C:8]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[C:10](=[O:17])[N:9]1[CH2:18][CH2:19][C@@H:20]([C@H:24]([OH:37])[CH2:25][CH2:26][C:27]1[CH:28]=[CH:29][C:30]([C:33]([F:35])([F:34])[F:36])=[CH:31][CH:32]=1)[C:21]([OH:23])=[O:22]

Participants

4

Reactant 2

HCID 11430Potassium CarbonateHCID 86700973(2S,3R)-2-[2-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)ethyl]-3-(formyloxy)-5-[4-(trifluoromethyl)phenyl]pentanoic acid

Product 1

HCID 25009034(2S,3R)-2-[2-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)ethyl]-3-hydroxy-5-[4-(trifluoromethyl)phenyl]pentanoic acid

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Potassium carbonate (0.178 g) was added to a solution of the compound obtained from step h above (0.2 g) in methanol (7 mL) at 0° C. The reaction mixture was stirred at room temperature for 3 hours. The solvents were evaporated, and the residue was taken into water and ethyl acetate. The organic layer was washed with water and brine solution, and dried over anhydrous sodium sulphate. The solvent was evaporated under reduced pressure to obtain a residue which was purified by column chromatography over silica gel using 10% methanol in dichloromethane as eluant to afford the title compound (0.090 g).

Workup

  1. customThe solvents were evaporated
  2. washThe organic layer was washed with water and brine solution
  3. dry with materialdried over anhydrous sodium sulphate
  4. customThe solvent was evaporated under reduced pressure
  5. customto obtain a residue which
  6. customwas purified by column chromatography over silica gel using 10% methanol in dichloromethane as eluant

Sources & evidence

ORD record
ord-14fa507a1abc477aa114b4597c5b308f
Source dataset
uspto-grants-2014_08
Patent number
US08816073B2

Reaction notes

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