Sodium Hydroxide → 2-Methyl-2-{2-methyl-4-[([4-(trifluoromethyl)benzyl]{6-[4-(trifluoromethyl)phenyl]pyridin-2-yl}amino)methyl]phenoxy}propanoic acid

HRID 1269671Notes

Reaction equation

HRID 1269671 reaction equation
[CH3:1][C:2]([O:9][C:10]1[CH:15]=[CH:14][C:13]([CH2:16][N:17]([CH2:34][C:35]2[CH:40]=[CH:39][C:38]([C:41]([F:44])([F:43])[F:42])=[CH:37][CH:36]=2)[C:18]2[CH:23]=[CH:22][CH:21]=[C:20]([C:24]3[CH:29]=[CH:28][C:27]([C:30]([F:33])([F:32])[F:31])=[CH:26][CH:25]=3)[N:19]=2)=[CH:12][C:11]=1[CH3:45])([CH3:8])[C:3]([O:5]CC)=[O:4].[OH-].[Na+]>O1CCCC1.CO>[CH3:8][C:2]([O:9][C:10]1[CH:15]=[CH:14][C:13]([CH2:16][N:17]([CH2:34][C:35]2[CH:40]=[CH:39][C:38]([C:41]([F:44])([F:43])[F:42])=[CH:37][CH:36]=2)[C:18]2[CH:23]=[CH:22][CH:21]=[C:20]([C:24]3[CH:29]=[CH:28][C:27]([C:30]([F:32])([F:31])[F:33])=[CH:26][CH:25]=3)[N:19]=2)=[CH:12][C:11]=1[CH3:45])([CH3:1])[C:3]([OH:5])=[O:4]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 18448414Ethyl 2-methyl-2-{2-methyl-4-[([4-(trifluoromethyl)benzyl]{6-[4-(trifluoromethyl)phenyl]pyridin-2-yl}amino)methyl]phenoxy}propanoate

Product 1

HCID 98088462-Methyl-2-{2-methyl-4-[([4-(trifluoromethyl)benzyl]{6-[4-(trifluoromethyl)phenyl]pyridin-2-yl}amino)methyl]phenoxy}propanoic acidYield 90.5%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of ethyl 2-methyl-2-{2-methyl-4-[([4-(trifluoromethyl)benzyl]{6-[4-(trifluoromethyl)phenyl]pyridin-2-yl}amino)methyl]phenoxy}propanoate (0.07 g, 0.11 mmol) in tetrahydrofuran (2 mL) and methanol (2 mL) was added 2M aq. NaOH (1 mL). The resulting solution was stirred at room temperature for 20 h then concentrated in vacuo. The residue was acidified with 2M HCl aq. and extracted with CH2Cl2 (2×30 mL). The combined organic extracts were dried (Na2SO4), filtered and evaporated to afford the title compound as a colourless oil (60 mg).

Workup

  1. concentrationthen concentrated in vacuo
  2. extractionextracted with CH2Cl2 (2×30 mL)
  3. dry with materialThe combined organic extracts were dried (Na2SO4)
  4. filtrationfiltered
  5. customevaporated

Sources & evidence

ORD record
ord-d4103b23f3b54eaeb8de177ed4b9fb8d
Source dataset
uspto-grants-2007_04
Patent number
US07199239B2

Reaction notes

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