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

HRID 1691934Notes

Reaction equation

HRID 1691934 reaction equation
C[O:2][C:3]([CH:5]1[CH2:10][CH2:9][N:8]([C:11]2[CH:16]=[CH:15][C:14]([NH:17][C:18]([C:20]3[N:21]=[C:22]([C:29]4[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=4)[O:23][C:24]=3[C:25]([F:28])([F:27])[F:26])=[O:19])=[CH:13][CH:12]=2)[CH2:7][CH2:6]1)=[O:4].[OH-].[Na+]>CO.C1COCC1>[C:29]1([C:22]2[O:23][C:24]([C:25]([F:26])([F:27])[F:28])=[C:20]([C:18]([NH:17][C:14]3[CH:13]=[CH:12][C:11]([N:8]4[CH2:7][CH2:6][CH:5]([C:3]([OH:4])=[O:2])[CH2:10][CH2:9]4)=[CH:16][CH:15]=3)=[O:19])[N:21]=2)[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 576520321-{4-[(2-Phenyl-5-trifluoromethyl-oxazole-4-carbonyl)-amino]-phenyl}-piperidine-4-carboxylic acid methyl ester

Product 1

HCID 576521231-{4-[(2-Phenyl-5-trifluoromethyl-oxazole-4-carbonyl)-amino]-phenyl}-piperidine-4-carboxylic acidYield 86%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

The above 1-{4-[(2-phenyl-5-trifluoromethyl-oxazole-4-carbonyl)-amino]-phenyl}-piperidine-4-carboxylic acid methyl ester (470 mg, 1 mmol) was dissolved in a mixture of methanol (7 mL) and THF (2 mL). To this solution was added 1N sodium hydroxide solution (3 mL). The mixture was stirred at room temperature for 4 hrs until all starting material was consumed. Solvents were evaporated and the residue was diluted with water (8 mL). The solution was filtered and the filtrate was acidified with 1N hydrochloric acid (3.5 mL). The yellow precipitate was filtered and dried in the air to give 1-{4-[(2-phenyl-5-trifluoromethyl-oxazole-4-carbonyl)-amino]-phenyl}-piperidine-4-carboxylic acid (395 mg). 1H-NMR is consistent with the desired structure. LC-MS indicated a single peak (Rf=3.23 min). LRMS for C23H20F3N3O4 (m/e) calcd 459.14, obsd 460.2 (M+1).

Workup

  1. customwas consumed
  2. customSolvents were evaporated
  3. additionthe residue was diluted with water (8 mL)
  4. filtrationThe solution was filtered
  5. filtrationThe yellow precipitate was filtered
  6. customdried in the air

Sources & evidence

ORD record
ord-8344934b0f48434695b9c91908e5cf48
Source dataset
uspto-grants-2012_04
Patent number
US08153644B2

Reaction notes

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