Potassium Carbonate → HCID 57857053, compound

HRID 561731Notes

Reaction equation

HRID 561731 reaction equation
C([O:9][C@@H:10]1[CH2:18][C@@H:13]2[O:14][C:15](=[O:17])[CH2:16][C@@H:12]2[C@H:11]1[CH2:19][CH2:20][C:21]([F:31])([F:30])[CH2:22][O:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)(=O)C1C=CC=CC=1.C(=O)([O-])[O-].[K+].[K+]>CO>[F:31][C:21]([F:30])([CH2:22][O:23][C:24]1[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=1)[CH2:20][CH2:19][C@@H:11]1[C@@H:12]2[C@@H:13]([O:14][C:15](=[O:17])[CH2:16]2)[CH2:18][C@H:10]1[OH:9]

Participants

4

Reactant 2

HCID 11430Potassium CarbonateHCID 57857035HCID 57857035, compound

Product 1

HCID 57857053HCID 57857053, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

(3aR,4R,5R,6aS)-4-(3,3-Difluoro-4-phenoxybutyl)-2-oxohexahydro-2H-cyclopenta[b]furan-5-yl benzoate (prepared in Step C, 1.0 g, 2.4 mmol) is dissolved in methanol (0.2 M) and potassium carbonate (194 mg, 1.41 mmol) is added. The reaction mixture is stirred at room temperature and the progress is monitored by TLC every 30 minutes. After complete consumption of starting material, the reaction mixture is acidified with 5% KHSO4 and diluted with brine. The product is extracted with ethyl acetate twice. The combined organic layers are dried over sodium sulfate, filtered and evaporated. The crude product is purified by flash chromatography on regular silica gel eluted with ethyl acetate-hexanes (1:1) to afford the title intermediate.

Workup

  1. customAfter complete consumption of starting material
  2. additiondiluted with brine
  3. extractionThe product is extracted with ethyl acetate twice
  4. dry with materialThe combined organic layers are dried over sodium sulfate
  5. filtrationfiltered
  6. customevaporated
  7. customThe crude product is purified by flash chromatography on regular silica gel
  8. washeluted with ethyl acetate-hexanes (1:1)

Sources & evidence

ORD record
ord-7407519c71f24aa9a989b77bd9760cb1
Source dataset
uspto-grants-2011_11
Patent number
US08063240B2

Reaction notes

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