Sodium Hydroxide → (2-(3-Methoxy-propyl)-4-{methyl-[2-methyl-6-(4-trifluoromethyl-phenyl)-pyridin-3-ylmethyl]-amino}-phenoxy)-acetic acid

HRID 1242284Notes

Reaction equation

HRID 1242284 reaction equation
C([O:3][C:4](=[O:38])[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[CH2:33][CH2:34][CH2:35][O:36][CH3:37])C.[OH-].[Na+]>C1COCC1.CCO>[CH3:37][O:36][CH2:35][CH2:34][CH2:33][C:8]1[CH:9]=[C:10]([N:13]([CH3:32])[CH2:14][C:15]2[C:16]([CH3:31])=[N:17][C:18]([C:21]3[CH:22]=[CH:23][C:24]([C:27]([F:30])([F:29])[F:28])=[CH:25][CH:26]=3)=[CH:19][CH:20]=2)[CH:11]=[CH:12][C:7]=1[O:6][CH2:5][C:4]([OH:38])=[O:3]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 67072320(2-(3-Methoxy-propyl)-4-{methyl-[2-methyl-6-(4-trifluoromethyl-phenyl)-pyridin-3-ylmethyl]-amino}-phenoxy)-acetic acid ethyl ester

Product 1

HCID 21935950(2-(3-Methoxy-propyl)-4-{methyl-[2-methyl-6-(4-trifluoromethyl-phenyl)-pyridin-3-ylmethyl]-amino}-phenoxy)-acetic acid

Reagents, catalysts & solvents 1

HCID 21873804Tetrahydrofuran ethanolSolvent

Procedure

0.125 g (0.24 mmol) of the above prepared (2-(3-methoxy-propyl)-4-{methyl-[2-methyl-6-(4-trifluoromethyl-phenyl)-pyridin-3-ylmethyl]-amino}-phenoxy)-acetic acid ethyl ester was dissolved in 1.44 ml of THF/EtOH=1/1, treated with 0.72 ml (3 eq.) of 1N NaOH, and kept at ambient temperature for 0.5 h. The reaction mixture was then poured onto crashed ice/AcOEt/HCl dil., the organic layer washed with water, dried over sodium sulfate, and evaporated to dryness. Crystallization from hexane/AcOEt produced finally 0.102 g of the title compound as off-white crystals of mp. 72–73° C.

Workup

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

Sources & evidence

ORD record
ord-15c3c89a912d4099858aa772aa44c730
Source dataset
uspto-grants-2006_10
Patent number
US07115611B2

Reaction notes

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