Tetrahydrofuran → 3-{4-[4-Ethyl-2-(4-trifluoromethyl-phenyl)-oxazol-5-ylmethoxy]-2-methyl-phenyl}-propionic acid

HRID 854558Notes

Reaction equation

HRID 854558 reaction equation
C[O:2][C:3](=[O:32])[CH2:4][CH2:5][C:6]1[CH:11]=[CH:10][C:9]([O:12][CH2:13][C:14]2[O:18][C:17]([C:19]3[CH:24]=[CH:23][C:22]([C:25]([F:28])([F:27])[F:26])=[CH:21][CH:20]=3)=[N:16][C:15]=2[CH2:29][CH3:30])=[CH:8][C:7]=1[CH3:31].[OH-].[Na+].C1COCC1>CO>[CH2:29]([C:15]1[N:16]=[C:17]([C:19]2[CH:20]=[CH:21][C:22]([C:25]([F:26])([F:27])[F:28])=[CH:23][CH:24]=2)[O:18][C:14]=1[CH2:13][O:12][C:9]1[CH:10]=[CH:11][C:6]([CH2:5][CH2:4][C:3]([OH:32])=[O:2])=[C:7]([CH3:31])[CH:8]=1)[CH3:30]

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 586266363-{4-[4-Ethyl-2-(4-trifluoromethyl-phenyl)-oxazol-5-ylmethoxy]-2-methyl-phenyl}-propionic acid methyl ester

Product 1

HCID 101948343-{4-[4-Ethyl-2-(4-trifluoromethyl-phenyl)-oxazol-5-ylmethoxy]-2-methyl-phenyl}-propionic acid

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

3-{4-[4-Ethyl-2-(4-trifluoromethyl-phenyl)-oxazol-5-ylmethoxy]-2-methyl-phenyl}-propionic acid methyl ester (0.100 g, 0.223 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+] 434 (M++H), 432 (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-65f509fbe6184388a410a3e78a98a226
Source dataset
uspto-grants-2007_08
Patent number
US07259175B2

Reaction notes

Loading…