Sodium Hydroxide → [Rac]-(2-methyl-4-{1-[2-methyl-6-(4-trifluoromethyl-phenyl)-pyridin-3-yl]-ethoxy}-phenylsulfanyl)-acetic acid

HRID 1242311Notes

Reaction equation

HRID 1242311 reaction equation
C([O:5][C:6](=[O:36])[CH2:7][S:8][C:9]1[CH:14]=[CH:13][C:12]([O:15][CH:16]([C:18]2[C:19]([CH3:34])=[N:20][C:21]([C:24]3[CH:29]=[CH:28][C:27]([C:30]([F:33])([F:32])[F:31])=[CH:26][CH:25]=3)=[CH:22][CH:23]=2)[CH3:17])=[CH:11][C:10]=1[CH3:35])(C)(C)C.[OH-].[Na+]>C1COCC1.CCO>[CH3:35][C:10]1[CH:11]=[C:12]([O:15][CH:16]([C:18]2[C:19]([CH3:34])=[N:20][C:21]([C:24]3[CH:29]=[CH:28][C:27]([C:30]([F:33])([F:31])[F:32])=[CH:26][CH:25]=3)=[CH:22][CH:23]=2)[CH3:17])[CH:13]=[CH:14][C:9]=1[S:8][CH2:7][C:6]([OH:36])=[O:5]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 69526547(2-Methyl-4-{1-[2-methyl-6-(4-trifluoromethyl-phenyl)-pyridin-3-yl]-ethoxy]-phenylsulfanyl)-acetic acid tert-butyl ester

Product 1

HCID 11305740[Rac]-(2-methyl-4-{1-[2-methyl-6-(4-trifluoromethyl-phenyl)-pyridin-3-yl]-ethoxy}-phenylsulfanyl)-acetic acid

Reagents, catalysts & solvents 1

HCID 21873804Tetrahydrofuran ethanolSolvent

Procedure

0.143 g (0.28 mmol) of the above prepared [rac]-(2-methyl-4-{1-[2-methyl-6-(4-trifluoromethyl-phenyl)-pyridin-3-yl]-ethoxy}-phenylsulfanyl)-acetic acid tert-butyl ester was dissolved in 2.75 ml of THF/EtOH=1/1, treated with 1.38 ml (3 eq.) of 1N NaOH and kept at ambient temperature for 5 h. The reaction mixture was then poured onto crashed ice/AcOEt/HCl dil., the organic layer was washed with water, dried over sodium sulfate, and evaporated to dryness to leave, since recrystallisation from AcOEt/hexane failed, 0.095 g of the title compound as colorless foam.

Workup

  1. additionThe reaction mixture was then poured
  2. washthe organic layer was washed with water
  3. dry with materialdried over sodium sulfate
  4. customevaporated to dryness
  5. customto leave, since recrystallisation from AcOEt/hexane

Sources & evidence

ORD record
ord-4def64f54ae6443fbcf94a3a9a1567fe
Source dataset
uspto-grants-2006_10
Patent number
US07115611B2

Reaction notes

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