Potassium Carbonate → (2S,3R)-5-(3',5'-difluorobiphenyl-4-yl)-2-[2-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)ethyl]-3-hydroxypentanoic acid

HRID 2410425Notes

Reaction equation

HRID 2410425 reaction equation
C(=O)([O-])[O-].[K+].[K+].[F:7][C:8]1[CH:9]=[C:10]([C:15]2[CH:20]=[CH:19][C:18]([CH2:21][CH2:22][C@@H:23]([O:41]C=O)[C@H:24]([CH2:28][CH2:29][N:30]3[C:38](=[O:39])[C:37]4[C:32](=[CH:33][CH:34]=[CH:35][CH:36]=4)[C:31]3=[O:40])[C:25]([OH:27])=[O:26])=[CH:17][CH:16]=2)[CH:11]=[C:12]([F:14])[CH:13]=1>CO>[F:14][C:12]1[CH:11]=[C:10]([C:15]2[CH:20]=[CH:19][C:18]([CH2:21][CH2:22][C@@H:23]([OH:41])[C@H:24]([CH2:28][CH2:29][N:30]3[C:31](=[O:40])[C:32]4[C:37](=[CH:36][CH:35]=[CH:34][CH:33]=4)[C:38]3=[O:39])[C:25]([OH:27])=[O:26])=[CH:17][CH:16]=2)[CH:9]=[C:8]([F:7])[CH:13]=1

Participants

4

Reactant 2

HCID 11430Potassium CarbonateHCID 86640488(2S,3R)-5-(3',5'-difluorobiphenyl-4-yl)-2-[2-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)ethyl]-3-(formyloxy)pentanoic acid

Product 1

HCID 67182195(2S,3R)-5-(3',5'-difluorobiphenyl-4-yl)-2-[2-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)ethyl]-3-hydroxypentanoic acid

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Potassium carbonate (0.06 g) was added to a solution of the compound obtained from step e above (0.12 g) in methanol (10 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 with preparatory thin layer chromatography using 10% methanol in ethyl acetate as eluent to get the title compound (0.025 gm).

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 with preparatory thin layer chromatography

Sources & evidence

ORD record
ord-ffa90d1a34544cf290ac26188de8b8be
Source dataset
uspto-grants-2014_08
Patent number
US08816073B2

Reaction notes

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