Sodium Hydroxide → [Rac]-[4-(methyl-{1-[2-methyl-6-(4-trifluoromethyl-phenyl)-pyridin-3-yl]-ethyl}-amino)-naphthalen-1-yloxy]-acetic acid

HRID 1726964Notes

Reaction equation

HRID 1726964 reaction equation
C([O:3][C:4](=[O:38])[CH2:5][O:6][C:7]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[C:10]([N:17]([CH3:37])[CH:18]([C:20]2[C:21]([CH3:36])=[N:22][C:23]([C:26]3[CH:31]=[CH:30][C:29]([C:32]([F:35])([F:34])[F:33])=[CH:28][CH:27]=3)=[CH:24][CH:25]=2)[CH3:19])=[CH:9][CH:8]=1)C.[OH-].[Na+]>C1COCC1.CCO>[CH3:37][N:17]([CH:18]([C:20]1[C:21]([CH3:36])=[N:22][C:23]([C:26]2[CH:27]=[CH:28][C:29]([C:32]([F:34])([F:35])[F:33])=[CH:30][CH:31]=2)=[CH:24][CH:25]=1)[CH3:19])[C:10]1[C:11]2[C:16](=[CH:15][CH:14]=[CH:13][CH:12]=2)[C:7]([O:6][CH2:5][C:4]([OH:38])=[O:3])=[CH:8][CH:9]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 69035155[Rac]-[4-(methyl-{1-[2-methyl-6-(4-trifluoromethyl-phenyl)-pyridin-3-yl]-ethyl}-amino)-naphthalen-1-yloxy]-acetic acid ethyl ester

Product 1

HCID 11202730[Rac]-[4-(methyl-{1-[2-methyl-6-(4-trifluoromethyl-phenyl)-pyridin-3-yl]-ethyl}-amino)-naphthalen-1-yloxy]-acetic acid

Reagents, catalysts & solvents 1

HCID 21873804Tetrahydrofuran ethanolSolvent

Procedure

0.055 g (0.11 mmol) of the above prepared [rac]-[4-(methyl-{1-[2-methyl-6-(4-trifluoromethyl-phenyl)-pyridin-3-yl]-ethyl}-amino)-naphthalen-1-yloxy]-acetic acid ethyl ester was dissolved in 0:6 ml of THF/EtOH=1/1, treated with 0.33 ml (3 eq.) of 1N NaOH, and kept at 0° C. for 2 h. The reaction mixture was then poured onto crashed ice/AcOEt/HCl dil., the organic layer washed with water and brine, dried over sodium sulfate, and evaporated to dryness. Crystallization from hexane/AcOEt afforded finally 0.040 g of the title compound as off-white solid of mp. 157-58° C.

Workup

  1. dissolutionwas dissolved in 0
  2. additionThe reaction mixture was then poured
  3. washthe organic layer washed with water and brine
  4. dry with materialdried over sodium sulfate
  5. customevaporated to dryness
  6. customCrystallization from hexane/AcOEt

Sources & evidence

ORD record
ord-ed5c13bd1e1b4b8690c2445838c80b82
Source dataset
uspto-grants-2009_02
Patent number
US07495001B2

Reaction notes

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