Tetrahydrofuran → 3-(4-{1-[4-Ethyl-2-(4-trifluoromethyl-phenyl)-oxazol-5-yl]-ethoxy}-2-methyl-phenyl)-propionic Acid

HRID 860662Notes

Reaction equation

HRID 860662 reaction equation
C[O:2][C:3](=[O:33])[CH2:4][CH2:5][C:6]1[CH:11]=[CH:10][C:9]([O:12][CH:13]([C:15]2[O:19][C:18]([C:20]3[CH:25]=[CH:24][C:23]([C:26]([F:29])([F:28])[F:27])=[CH:22][CH:21]=3)=[N:17][C:16]=2[CH2:30][CH3:31])[CH3:14])=[CH:8][C:7]=1[CH3:32].[OH-].[Na+].C1COCC1>CO>[CH2:30]([C:16]1[N:17]=[C:18]([C:20]2[CH:25]=[CH:24][C:23]([C:26]([F:27])([F:28])[F:29])=[CH:22][CH:21]=2)[O:19][C:15]=1[CH:13]([O:12][C:9]1[CH:10]=[CH:11][C:6]([CH2:5][CH2:4][C:3]([OH:33])=[O:2])=[C:7]([CH3:32])[CH:8]=1)[CH3:14])[CH3:31]

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 102885253-(4-{1-[4-Ethyl-2-(4-trifluoromethyl-phenyl)-oxazol-5-yl]-ethoxy}-2-methyl-phenyl)-propionic Acid Methyl Ester

Product 1

HCID 102169303-(4-{1-[4-Ethyl-2-(4-trifluoromethyl-phenyl)-oxazol-5-yl]-ethoxy}-2-methyl-phenyl)-propionic Acid

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

3-(4-{1-[4-Ethyl-2-(4-trifluoromethyl-phenyl)-oxazol-5-yl]-ethoxy}-2-methyl-phenyl)-propionic acid methyl ester (0.095 g, 0.206 mmole) is treated with a mixture of NaOH(aq) (1 mL)/THF (3 mL)/MeOH (3 mL) at room temperature overnight. The organic solvents are removed on rota-vapor. The residue is diluted with water (10 mL), acidified to pH=2 with 6N HCl(aq). The precipitate is collected through filtration, washed with cold water (30 mL) and dried to provide the titled compound as a white solid. Mass [EI+] 448 (M++H), 446 (M+−H).

Workup

  1. customThe organic solvents are removed on rota-vapor
  2. additionThe residue is diluted with water (10 mL)
  3. filtrationThe precipitate is collected through filtration
  4. washwashed with cold water (30 mL)
  5. customdried

Sources & evidence

ORD record
ord-59dd953027254b8d9eb790b931db0255
Source dataset
uspto-grants-2006_12
Patent number
US07153878B2

Reaction notes

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