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

HRID 490777

Reaction equation

HRID 490777 reaction equation
C[O:2][C:3](=[O:30])[CH2:4][CH2:5][C:6]1[CH:11]=[CH:10][C:9]([O:12][CH2:13][C:14]2[S:15][C:16]([C:19]3[CH:24]=[CH:23][C:22]([C:25]([F:28])([F:27])[F:26])=[CH:21][CH:20]=3)=[CH:17][CH:18]=2)=[CH:8][C:7]=1[CH3:29].[OH-].[Na+].[CH2:33]1COCC1>CO>[CH3:29][C:7]1[CH:8]=[C:9]([O:12][CH2:13][C:14]2[S:15][C:16]([C:19]3[CH:24]=[CH:23][C:22]([C:25]([F:27])([F:26])[F:28])=[CH:21][CH:20]=3)=[CH:17][C:18]=2[CH3:33])[CH:10]=[CH:11][C:6]=1[CH2:5][CH2:4][C:3]([OH:2])=[O:30]

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 688530103-{2-Methyl-4-[5-(4-trifluoromethyl-phenyl)-thiophen-2-ylmethoxy]-phenyl}-propionic acid methyl ester

Product 1

HCID 101600493-{2-Methyl-4-[3-methyl-5-(4-trifluoromethyl-phenyl)-thiophen-2-ylmethoxy]-phenyl}-propionic acid

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

3-{2-Methyl-4-[5-(4-trifluoromethyl-phenyl)-thiophen-2-ylmethoxy]-phenyl}-propionic acid methyl ester (0.043 g, 0.0959 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. MS (ES): 433 (M+H); the structure is also confirmed by proton NMR. A substantially similar process is used to make the following compound and the Compound of Example 45, below.

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-a88cd4decb104f5f9b7d73e661c3e3b6
Source dataset
uspto-grants-2009_05
Patent number
US07528160B2

Linked notes

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