Sodium Hydroxide → 6-[(3R,4R)-4-[(4-Chlorobenzoyl)methylamino]-3-(3,4-dichlorophenyl)-1-piperidinyl]-3-pyridinecarboxylic acid

HRID 1260973Notes

Reaction equation

HRID 1260973 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([N:10]([CH3:36])[C@@H:11]2[CH2:16][CH2:15][N:14]([C:17]3[N:22]=[CH:21][C:20]([C:23]([O:25]CC)=[O:24])=[CH:19][CH:18]=3)[CH2:13][C@H:12]2[C:28]2[CH:33]=[CH:32][C:31]([Cl:34])=[C:30]([Cl:35])[CH:29]=2)=[O:9])=[CH:4][CH:3]=1.[OH-].[Na+]>CO>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([N:10]([CH3:36])[C@@H:11]2[CH2:16][CH2:15][N:14]([C:17]3[N:22]=[CH:21][C:20]([C:23]([OH:25])=[O:24])=[CH:19][CH:18]=3)[CH2:13][C@H:12]2[C:28]2[CH:33]=[CH:32][C:31]([Cl:34])=[C:30]([Cl:35])[CH:29]=2)=[O:9])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 68935710HCID 68935710, compound

Product 1

HCID 689390336-[(3R,4R)-4-[(4-Chlorobenzoyl)methylamino]-3-(3,4-dichlorophenyl)-1-piperidinyl]-3-pyridinecarboxylic acidYield 100%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of the compound (0.500 g) obtained in Example 478 in methanol (6 mL) was added 1N aqueous sodium hydroxide solution (2.74 mL), and the mixture was stirred for 10 hr. The reaction mixture was concentrated, the residue was made neutral with 1N hydrochloric acid, and the resultant product was extracted with ethyl acetate. The organic layer was washed with brine and dried, and the solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography (solvent gradient; 30→100% ethyl acetate/hexane) to give the title compound (0.474 g, 100%) as a white powder.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. extractionthe resultant product was extracted with ethyl acetate
  3. washThe organic layer was washed with brine
  4. customdried
  5. customthe solvent was evaporated under reduced pressure
  6. customThe obtained residue was purified by silica gel column chromatography (solvent gradient; 30→100% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-60c597cc8b234070873b571e6676a9cd
Source dataset
uspto-grants-2013_06
Patent number
US08470816B2

Reaction notes

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