Tetrahydrofuran → 5-[4-(2-Trifluoromethyl-phenyl)-oxazol-2-yl]-pentanoic acid

HRID 1443754Notes

Reaction equation

HRID 1443754 reaction equation
C[O:2][C:3](=[O:23])[CH2:4][CH2:5][CH2:6][CH2:7][C:8]1[O:9][CH:10]=[C:11]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2[C:19]([F:22])([F:21])[F:20])[N:12]=1.C1COCC1.[OH-].[Na+]>CCO>[F:21][C:19]([F:20])([F:22])[C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=1[C:11]1[N:12]=[C:8]([CH2:7][CH2:6][CH2:5][CH2:4][C:3]([OH:23])=[O:2])[O:9][CH:10]=1

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 591677795-[4-(2-Trifluoromethyl-phenyl)-oxazol-2-yl]-pentanoic acid methyl ester

Product 1

HCID 684926205-[4-(2-Trifluoromethyl-phenyl)-oxazol-2-yl]-pentanoic acid

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Combine 5-[4-(2-trifluoromethyl-phenyl)-oxazol-2-yl]-pentanoic acid methyl ester (3.35 g, 9.9 mmol) with THF (3 mL), EtOH (3 mL) and 2N NaOH (15 mL) and stir until hydrolysis is complete. Concentrate the mixture, dilute the residue with water and adjust the pH to 3.0-4.0 using aq HCl. Extract the mixture with EtOAc and dry the extracts over Na2SO4 before concentrating. Chromatograph the residue over silica gel (MeOH/CH2Cl2) to allow for recovery of 5-[4-(2-trifluoromethyl-phenyl)-oxazol-2-yl]-pentanoic acid (2.36 g, 76%). MS (ES): (M+1)+ 314.2 m/z.

Workup

  1. concentrationConcentrate the mixture
  2. additiondilute the residue with water
  3. extractionExtract the mixture with EtOAc
  4. dry with materialdry the extracts over Na2SO4
  5. concentrationbefore concentrating

Sources & evidence

ORD record
ord-cce1296abd414079a6b52dd1cedb3f92
Source dataset
uspto-grants-2010_02
Patent number
US07662771B2

Reaction notes

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