Sodium Hydroxide → HCID 10390097, compound

HRID 2193489Notes

Reaction equation

HRID 2193489 reaction equation
[CH3:1][O:2][C:3](=[O:35])[C:4]1[CH:34]=[CH:33][C:7]([C:8]([NH:10][CH:11]2[CH2:16][CH2:15][CH:14]([O:17][C:18](=[O:20])[CH3:19])[CH2:13][CH:12]2[C:21]2[CH:26]=[CH:25][C:24]([O:27][CH3:28])=[C:23]([O:29][CH:30]([F:32])[F:31])[CH:22]=2)=O)=[CH:6][CH:5]=1.[OH-].[Na+]>P(Cl)(Cl)(Cl)=O.ClCCl>[CH3:1][O:2][C:3](=[O:35])[C:4]1[CH:34]=[CH:33][C:7]([C:8]2[C:26]3[C:21](=[CH:22][C:23]([O:29][CH:30]([F:32])[F:31])=[C:24]([O:27][CH3:28])[CH:25]=3)[CH:12]3[CH:11]([CH2:16][CH2:15][CH:14]([O:17][C:18](=[O:20])[CH3:19])[CH2:13]3)[N:10]=2)=[CH:6][CH:5]=1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 68655397HCID 68655397, compound2×

Product 1

HCID 10390097HCID 10390097, compoundYield 64.4%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 24813Phosphorus oxychlorideSolvent

Conditions

Temperature
100 °C

Procedure

500 mg of N-{(1RS,2RS,4RS)-4-acetoxy-2-[3-(1,1-difluoro-methoxy)-4-methoxy-phenyl]-cyclohexyl}-terephthalamic acid methyl ester (compound D2) are dissolved in 2 ml of phosphorus oxychloride and heated for 4.5 h at 100° C. After cooling to room temperature the sample is diluted with 10 ml of dichloromethane and added dropwise to an aqueous sodium hydroxide solution. The water layer is extracted twice with dichloromethane. The solvent is removed and the crude product purified by chromatography on silica gel to give 310 mg of the title compound as a colourless foam.

Workup

  1. temperatureAfter cooling to room temperature the sample
  2. extractionThe water layer is extracted twice with dichloromethane
  3. customThe solvent is removed
  4. customthe crude product purified by chromatography on silica gel

Sources & evidence

ORD record
ord-85ca0e21ee8746ceafaecd402b26590f
Source dataset
uspto-grants-2012_12
Patent number
US08329906B2

Reaction notes

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