Sodium Hydroxide → HCID 21935783, compound

HRID 1242303Notes

Reaction equation

HRID 1242303 reaction equation
C([O:3][C:4](=[O:37])[CH2:5][O:6][C:7]1[CH:12]=[CH:11][C:10]([N:13]([CH3:32])[CH2:14][C:15]2[C:16]([CH3:31])=[N:17][C:18]([C:21]3[CH:26]=[CH:25][C:24]([C:27]([F:30])([F:29])[F:28])=[CH:23][CH:22]=3)=[CH:19][CH:20]=2)=[CH:9][C:8]=1[C:33]([F:36])([F:35])[F:34])C.[OH-].[Na+]>C1COCC1.CCO>[CH3:32][N:13]([CH2:14][C:15]1[C:16]([CH3:31])=[N:17][C:18]([C:21]2[CH:22]=[CH:23][C:24]([C:27]([F:30])([F:28])[F:29])=[CH:25][CH:26]=2)=[CH:19][CH:20]=1)[C:10]1[CH:11]=[CH:12][C:7]([O:6][CH2:5][C:4]([OH:37])=[O:3])=[C:8]([C:33]([F:34])([F:35])[F:36])[CH:9]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 87258798HCID 87258798, compound

Product 1

HCID 21935783HCID 21935783, compound

Reagents, catalysts & solvents 1

HCID 21873804Tetrahydrofuran ethanolSolvent

Procedure

0.046 g (0.087 mmol) of the above prepared [rac]-(4-{methyl-[2-methyl-6-(4-trifluoromethyl-phenyl)-pyridin-3-ylmethyl]-amino}-2-trifluoromethyl-phenoxy)-acetic acid ethyl ester was dissolved in 0.52 ml of THF/EtOH=1/1, treated with 0.26 ml (3 eq.) of 1N NaOH and kept at ambient temperature for 3.5 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, after recrystallisation from AcOEt/hexane, 0.039 g of the title compound as off-white solid.

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
  6. customafter recrystallisation from AcOEt/hexane, 0.039 g of the title compound as off-white solid

Sources & evidence

ORD record
ord-6e87621c569942598618fe28f67a29a1
Source dataset
uspto-grants-2006_10
Patent number
US07115611B2

Reaction notes

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