Ethyl 2-(1-piperidinyl)-4-(trifluoromethyl)oxazole-5-carboxylate → HCID 57461778, compound

HRID 1020339Notes

Reaction equation

HRID 1020339 reaction equation
[N:1]1([C:7]2[O:8][C:9]([C:16]([O:18]CC)=[O:17])=[C:10]([C:12]([F:15])([F:14])[F:13])[N:11]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1>C1COCC1.O.[OH-].[Na+]>[N:1]1([C:7]2[O:8][C:9]([C:16]([OH:18])=[O:17])=[C:10]([C:12]([F:14])([F:15])[F:13])[N:11]=2)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

5

Reactant 1

HCID 57461777Ethyl 2-(1-piperidinyl)-4-(trifluoromethyl)oxazole-5-carboxylate

Product 1

HCID 57461778HCID 57461778, compoundYield 100.2%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolventHCID 14798Sodium HydroxideSolvent2×

Procedure

To a solution of ethyl 2-(1-piperidinyl)-4-trifluoromethyloxazole-5-carboxylate (A-3) (1.28 g) in THF (20 mL) at RT was added 1 N NaOH (20 mL). The reaction mixture was stirred at RT for 3 h then diluted with H2O (100 mL) and 1 N NaOH (10 mL). The aqueous solution was washed with Et2O (2×100 mL) and then acidified to pH=1 by addition of 1 N HCl, and extracted with EtOAc (3×50 mL). The combined organic extract was dried over Na2SO4, filtered, and concentrated to yield 2-(1-piperidinyl)-4-trifluoromethyloxazole-5-carboxylic acid (A-4) as a white solid (1.16 g, 100% yield). LCMS (ESI) calcd for [M+1]+ 265.1. found 265.1.

Workup

  1. washThe aqueous solution was washed with Et2O (2×100 mL)
  2. additionacidified to pH=1 by addition of 1 N HCl
  3. extractionextracted with EtOAc (3×50 mL)
  4. extractionThe combined organic extract
  5. dry with materialwas dried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-a6ddf7d4afcd4dd78a8407c39f6a1816
Source dataset
uspto-grants-2014_05
Patent number
US08716312B2

Reaction notes

Loading…