HCID 23564193, compound → HCID 18670439, compound

HRID 1059322Notes

Reaction equation

HRID 1059322 reaction equation
[CH2:1]([O:8][C:9]([N:11]1[CH2:16][CH2:15][CH:14]([C:17]2[CH:18]=[C:19]([CH2:23][CH:24]=[O:25])[CH:20]=[CH:21][CH:22]=2)[CH2:13][CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.P([O-])(O)(O)=[O:27].[Na+].Cl([O-])=O.[Na+]>O.CS(C)=O>[CH2:1]([O:8][C:9]([N:11]1[CH2:12][CH2:13][CH:14]([C:17]2[CH:18]=[C:19]([CH2:23][C:24]([OH:27])=[O:25])[CH:20]=[CH:21][CH:22]=2)[CH2:15][CH2:16]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 23564193HCID 23564193, compoundHCID 23668197Sodium ChloriteHCID 23672064Monosodium phosphate

Product 1

HCID 18670439HCID 18670439, compoundYield 95.5%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent3×

Procedure

To a solution of 2.0 g of 3-[1-(benzyloxycarbonyl)-piperidin-4-yl]phenylacetaldehyde and 1.0 g of sodium dihydrogenphosphate in 10 ml of water and 50 ml of dimethyl sulfoxide was added a solution of 2.0 g of sodium chlorite in water (10 ml) and the resulting mixture was reacted at room temperature for 20 minutes. After adding water, the reaction mixture was extracted with ethyl acetate, washed with a saturated aqueous solution of sodium chloride and dried over anhydrous magnesium sulfate. After distilling off the solvent under reduced pressure, 2.0 g of crude 3-[1-(benzyloxycarbonyl)piperidin-4-yl]phenylacetic acid was obtained as a colorless oily substance. To a solution of 2.0 g of this oily substance in 50 ml of methanol was added 0.47 ml of thionyl chloride at 0° C. and the resulting mixture was reacted at room temperature for 2 hours. The reaction mixture was distilled off under reduced pressure and the residue was purified by silica gel column chromatography (eluted with n-hexane/ethyl acetate) to thereby give 1.2 g of the title compound as a yellow oily substance.

Workup

  1. customthe resulting mixture was reacted at room temperature for 20 minutes
  2. extractionthe reaction mixture was extracted with ethyl acetate
  3. washwashed with a saturated aqueous solution of sodium chloride
  4. dry with materialdried over anhydrous magnesium sulfate
  5. distillationAfter distilling off the solvent under reduced pressure

Sources & evidence

ORD record
ord-7a5c6191a6134129aa8846ec84f0c9da
Source dataset
uspto-grants-2003_02
Patent number
US06518423B1

Reaction notes

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