Potassium Bicarbonate → HCID 68514790, compound

HRID 2042002Notes

Reaction equation

HRID 2042002 reaction equation
[C:1]([C:5]1[CH:24]=[C:23]([F:25])[CH:22]=[CH:21][C:6]=1[O:7][CH2:8][CH:9]1[CH2:13][CH2:12][N:11]([C:14](=[O:20])[CH2:15][CH2:16][C:17]([OH:19])=[O:18])[CH2:10]1)([CH3:4])([CH3:3])[CH3:2].C(=O)([O-])O.[K+].[Cl-].[Ca+2:32].[Cl-]>CO>[C:1]([C:5]1[CH:24]=[C:23]([F:25])[CH:22]=[CH:21][C:6]=1[O:7][CH2:8][CH:9]1[CH2:13][CH2:12][N:11]([C:14](=[O:20])[CH2:15][CH2:16][C:17]([O-:19])=[O:18])[CH2:10]1)([CH3:4])([CH3:2])[CH3:3].[C:1]([C:5]1[CH:24]=[C:23]([F:25])[CH:22]=[CH:21][C:6]=1[O:7][CH2:8][CH:9]1[CH2:13][CH2:12][N:11]([C:14](=[O:20])[CH2:15][CH2:16][C:17]([O-:19])=[O:18])[CH2:10]1)([CH3:4])([CH3:2])[CH3:3].[Ca+2:32]

Participants

5

Reactant 3

HCID 516893Potassium BicarbonateHCID 5284359Calcium ChlorideHCID 59577225HCID 59577225, compound

Product 1

HCID 68514790HCID 68514790, compoundYield 90.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 4-{3-[(2-tert-butyl-4-fluorophenoxy)methyl]pyrrolidin-1-yl}-4-oxobutanoic acid (260 mg, 0.74 mmol) obtained in Example 217 in methanol (10 mL) was added aqueous solution (10 mL) of potassium hydrogen carbonate (78 mg, 0.78 mmol). The reaction mixture was concentrated under reduced pressure, the residue was dissolved in methanol (10 mL), and aqueous solution (10 mL) of calcium chloride (43 g, 0.39 mmol) was added. The reaction mixture was concentrated under reduced pressure, and the residue was diluted with THF. The resulting precipitate was filtered, and the filtrate was concentrated to give the title compound (248 mg, 90%) as a white solid.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. dissolutionthe residue was dissolved in methanol (10 mL)
  3. concentrationThe reaction mixture was concentrated under reduced pressure
  4. additionthe residue was diluted with THF
  5. filtrationThe resulting precipitate was filtered
  6. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-714fbaaa7dcd422586ec77a0356e0924
Source dataset
uspto-grants-2013_11
Patent number
US08586571B2

Reaction notes

Loading…