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

HRID 1242309Notes

Reaction equation

HRID 1242309 reaction equation
C([O:5][C:6](=[O:36])[CH2:7][O:8][C:9]1[CH:14]=[CH:13][C:12]([S: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]([S: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:13]=[CH:14][C:9]=1[O:8][CH2:7][C:6]([OH:36])=[O:5]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 67072330(2-Methyl-4-{1-[2-methyl-6-(4-trifluoromethyl-phenyl)-pyridin-3-yl]-ethylsulfanyl}-phenoxy)-acetic acid tert-butyl ester

Product 1

HCID 11775564[Rac]-(2-methyl-4-{1-[2-methyl-6-(4-trifluoromethyl-phenyl)-pyridin-3-yl]-ethylsulfanyl}-phenoxy)-acetic acid

Reagents, catalysts & solvents 1

HCID 21873804Tetrahydrofuran ethanolSolvent

Procedure

0.322 g (0.62 mmol) of the above prepared (2-methyl-4-{1-[2-methyl-6-(4-trifluoromethyl-phenyl)-pyridin-3-yl]-ethylsulfanyl}-phenoxy)-acetic acid tert-butyl ester, containing some methyl ester, was dissolved in 3.8 ml of THF/EtOH=1/1, treated with 1.87 ml (3 eq.) of 1N NaOH, and kept at ambient temperature for 2 h. The reaction mixture was then poured onto crashed ice/HCl dil., extracted twice with AcOEt, washed with water, dried over sodium sulfate, and evaporated to dryness to leave, after crystallization from AcOEt/hexane, 0.276 g of the title compound as off-white solid of mp. 115–117° C.

Workup

  1. additionThe reaction mixture was then poured
  2. extractionextracted twice with AcOEt
  3. washwashed with water
  4. dry with materialdried over sodium sulfate
  5. customevaporated to dryness
  6. customto leave
  7. customafter crystallization from AcOEt/hexane, 0.276 g of the title compound as off-white solid of mp. 115–117° C.

Sources & evidence

ORD record
ord-53beb274cebe4470ad113d745e1b8380
Source dataset
uspto-grants-2006_10
Patent number
US07115611B2

Reaction notes

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