Lithium Hydroxide → 3-[3,5-Difluoro-4-(2-isopropylsulfanyl-pyridin-3-ylmethoxy)-phenyl]-propionic acid

HRID 62920Notes

Reaction equation

HRID 62920 reaction equation
C([O:3][C:4](=[O:27])[CH2:5][CH2:6][C:7]1[CH:12]=[C:11]([F:13])[C:10]([O:14][CH2:15][C:16]2[C:17]([S:22][CH:23]([CH3:25])[CH3:24])=[N:18][CH:19]=[CH:20][CH:21]=2)=[C:9]([F:26])[CH:8]=1)C.[OH-].[Li+]>C1COCC1.CO.O>[F:26][C:9]1[CH:8]=[C:7]([CH2:6][CH2:5][C:4]([OH:27])=[O:3])[CH:12]=[C:11]([F:13])[C:10]=1[O:14][CH2:15][C:16]1[C:17]([S:22][CH:23]([CH3:25])[CH3:24])=[N:18][CH:19]=[CH:20][CH:21]=1

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 90118180HCID 90118180, compound

Product 1

HCID 742221153-[3,5-Difluoro-4-(2-isopropylsulfanyl-pyridin-3-ylmethoxy)-phenyl]-propionic acidYield 91.3%

Reagents, catalysts & solvents 1

HCID 21892291Methanol tetrahydrofuran waterSolvent

Procedure

After 3-[3,5-difluoro-4-(2-isopropylsulfanyl-pyridin-3-ylmethoxy)phenyl]-propionic acid ethyl ester (66 mg, 0.167 mmol) obtained in Step A was dissolved in THF/MeOH/water (2:2:1, 5 mL), lithium hydroxide (12 mg, 0.50 mmol) was added thereto, and the mixture was stirred at room temperature for 2 hours. After the termination of the reaction, the reactant was concentrated under reduced pressure, and the residue was diluted with water. The aqueous layer was added with diethyl ether, stirred, and then extracted. The aqueous layer was added with 1N HCl to adjust pH to 2˜3, and then extracted with EtOAc. The organic layer was dried with MgSO4, and concentrated under reduced pressure to obtain the title compound (56 mg, 91%).

Workup

  1. customAfter the termination of the reaction
  2. concentrationthe reactant was concentrated under reduced pressure
  3. additionthe residue was diluted with water
  4. additionThe aqueous layer was added with diethyl ether
  5. stirringstirred
  6. extractionextracted
  7. additionThe aqueous layer was added with 1N HCl
  8. extractionextracted with EtOAc
  9. dry with materialThe organic layer was dried with MgSO4
  10. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-c337f1ec19ba43a3a3c333ed971ca393
Source dataset
uspto-grants-2016_09
Patent number
US09447044B2

Reaction notes

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