Sodium Hydroxide → 1-{4-[(2-Phenyl-5-trifluoromethyl-oxazole-4-carbonyl)-amino]-phenyl}-piperidine-4-carboxylic acid

HRID 1510269Notes

Reaction equation

HRID 1510269 reaction equation
C([O:3][C:4]([CH:6]1[CH2:11][CH2:10][N:9]([C:12]2[CH:17]=[CH:16][C:15]([NH:18][C:19]([C:21]3[N:22]=[C:23]([C:30]4[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=4)[O:24][C:25]=3[C:26]([F:29])([F:28])[F:27])=[O:20])=[CH:14][CH:13]=2)[CH2:8][CH2:7]1)=[O:5])C.[OH-].[Na+]>CO>[C:30]1([C:23]2[O:24][C:25]([C:26]([F:27])([F:28])[F:29])=[C:21]([C:19]([NH:18][C:15]3[CH:14]=[CH:13][C:12]([N:9]4[CH2:8][CH2:7][CH:6]([C:4]([OH:5])=[O:3])[CH2:11][CH2:10]4)=[CH:17][CH:16]=3)=[O:20])[N:22]=2)[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 576521271-{4-[(2-Phenyl-5-trifluoromethyl-oxazole-4-carbonyl)-amino]-phenyl}-piperidine-4-carboxylic acid ethyl ester

Product 1

HCID 576521231-{4-[(2-Phenyl-5-trifluoromethyl-oxazole-4-carbonyl)-amino]-phenyl}-piperidine-4-carboxylic acidYield 77.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 1-{4-[(2-phenyl-5-trifluoromethyl-oxazole-4-carbonyl)-amino]-phenyl}-piperidine-4-carboxylic acid ethyl ester (1.1 g, 2.3 mmol) in 20 mL of MeOH was treated with 2.8 mL (5.6 mmol) of 2 N NaOH, and the reaction mixture was stirred at room temperature overnight. The resulting mixture was then concentrated to remove most of the MeOH solvent. The residue was then neutralized with concentrated HCl. A white precipitate formed. The product was then collected by filtration, washed with water, triturated with ether, and dried to furnish 0.82 g of 1-{4-[(2-phenyl-5-trifluoromethyl-oxazole-4-carbonyl)-amino]-phenyl}-piperidine-4-carboxylic acid. This material was used in the next step without further purification.

Workup

  1. concentrationThe resulting mixture was then concentrated
  2. customto remove most of the MeOH solvent
  3. customA white precipitate formed
  4. filtrationThe product was then collected by filtration
  5. washwashed with water
  6. customtriturated with ether
  7. customdried

Sources & evidence

ORD record
ord-f11f89c525524c439b48764bbe76f897
Source dataset
uspto-grants-2012_07
Patent number
US08211914B2

Reaction notes

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