Lithium Hydroxide → HCID 11318176, compound

HRID 1726981Notes

Reaction equation

HRID 1726981 reaction equation
C[O:2][C:3](=[O:38])[CH:4]([O:36][CH3:37])[CH2:5][C:6]1[CH:15]=[C:14]([O:16][CH2:17][CH2:18][C:19]2[C:20]([CH3:35])=[N:21][C:22]([C:25]3[CH:30]=[CH:29][C:28]([C:31]([F:34])([F:33])[F:32])=[CH:27][CH:26]=3)=[CH:23][CH:24]=2)[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[CH:7]=1.[Li+].[OH-]>C1COCC1.CO>[CH3:37][O:36][CH:4]([CH2:5][C:6]1[CH:15]=[C:14]([O:16][CH2:17][CH2:18][C:19]2[C:20]([CH3:35])=[N:21][C:22]([C:25]3[CH:30]=[CH:29][C:28]([C:31]([F:32])([F:34])[F:33])=[CH:27][CH:26]=3)=[CH:23][CH:24]=2)[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[CH:7]=1)[C:3]([OH:38])=[O:2]

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 69036617HCID 69036617, compound

Product 1

HCID 11318176HCID 11318176, compound

Reagents, catalysts & solvents 1

HCID 21899815MeOH tetrahydrofuranSolvent

Procedure

0.43 g (0.82 mmol) of the above prepared [rac]-2-methoxy-3-(4-{2-[2-methyl-6-(4-trifluoromethyl-phenyl)-pyridin-3-yl]-ethoxy}-naphthalen-2-yl)-propionic acid methyl ester was dissolved in 15 ml of THF/MeOH (2:1); to the stirred solution was then added 1.64 ml of LiOH-solution (1 molar in water). After one hour, the reaction mixture was poured onto crashed ice/HCl and extracted twice with CH2Cl2; the organic layers were washed with water, dried over magnesium sulfate, filtered and evaporated. The residue was purified by chromatography [SiO2, CH2Cl2/MeOH (0 to 5% MeOH)] to give 0.42 g of pure title compound as light yellow solid.

Workup

  1. additionthe reaction mixture was poured
  2. extractionextracted twice with CH2Cl2
  3. washthe organic layers were washed with water
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. customevaporated
  7. customThe residue was purified by chromatography [SiO2, CH2Cl2/MeOH (0 to 5% MeOH)]

Sources & evidence

ORD record
ord-fc19550b98814adcba266e99e4336d3f
Source dataset
uspto-grants-2009_02
Patent number
US07495001B2

Reaction notes

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