Lithium Hydroxide → (2-Methyl-4-{methyl-[4-methyl-2-(4-trifluoromethyl-phenyl)-thiazol-5-ylmethyl]-amino}-phenoxy)-acetic acid

HRID 1393074Notes

Reaction equation

HRID 1393074 reaction equation
C([O:3][C:4](=[O:33])[CH2:5][O:6][C:7]1[CH:12]=[CH:11][C:10]([N:13]([CH3:31])[CH2:14][C:15]2[S: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[CH3:30])=[CH:9][C:8]=1[CH3:32])C.[Li+].[OH-].OS([O-])(=O)=O.[K+]>C1COCC1.CCO>[CH3:32][C:8]1[CH:9]=[C:10]([N:13]([CH3:31])[CH2:14][C:15]2[S:19][C:18]([C:20]3[CH:21]=[CH:22][C:23]([C:26]([F:28])([F:27])[F:29])=[CH:24][CH:25]=3)=[N:17][C:16]=2[CH3:30])[CH:11]=[CH:12][C:7]=1[O:6][CH2:5][C:4]([OH:33])=[O:3]

Participants

5

Reactant 3

HCID 3939Lithium HydroxideHCID 516920Potassium bisulfateHCID 69217871(2-Methyl-4-{methyl-[4-methyl-2-(4-trifluoromethyl-phenyl)-thiazol-5-ylmethyl]-amino}-phenoxy)-acetic acid ethyl ester

Product 1

HCID 11465092(2-Methyl-4-{methyl-[4-methyl-2-(4-trifluoromethyl-phenyl)-thiazol-5-ylmethyl]-amino}-phenoxy)-acetic acidYield 82.2%

Reagents, catalysts & solvents 1

HCID 21873804Tetrahydrofuran ethanolSolvent

Procedure

A solution of crude (2-methyl-4-{methyl-[4-methyl-2-(4-trifluoromethyl-phenyl)-thiazol-5-ylmethyl]-amino}-phenoxy)-acetic acid ethyl ester (0.84 g containing 0.74 g, 1.54 mmol) in THF/EtOH (9.2 ml, 1:1) were treated at 0° C. with 1M LiOH (4.6 ml, 4.6 mmol) for 2 min. After 2 h at RT, the solution was acidified by adding aqueous 10% KHSO4, and the mixture was extracted with Et2O (3×). The organic phase was washed with aqueous 10% NaCl, dried over Na2SO4 and evaporated. Crystallization (CH2Cl2/Et2O) gave 0.57 g (82%) (2-methyl-4-{methyl-[4-methyl-2-(4-trifluoromethyl-phenyl)-thiazol-5-ylmethyl]-amino}-phenoxy)-acetic acid as light yellow powder, MS: 449 (M-H)−, MP: 146-149° C., dec.

Workup

  1. extractionthe mixture was extracted with Et2O (3×)
  2. washThe organic phase was washed with aqueous 10% NaCl
  3. dry with materialdried over Na2SO4
  4. customevaporated
  5. customCrystallization (CH2Cl2/Et2O)

Sources & evidence

ORD record
ord-426a9e11d1ea494da3b68d746ba5357e
Source dataset
uspto-grants-2008_03
Patent number
US07345067B2

Reaction notes

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