Hydrochloric Acid → HCID 22262162, compound

HRID 1610508Notes

Reaction equation

HRID 1610508 reaction equation
[F:1][C:2]1[N:7]=[C:6]([CH:8]([OH:29])[CH:9]([CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([O:22][C:23]([F:28])([F:27])[CH:24]([F:26])[F:25])[CH:17]=2)[C:10]([O:12]CC)=[O:11])[CH:5]=[CH:4][CH:3]=1.[OH-].[Na+].Cl>CO>[F:1][C:2]1[N:7]=[C:6]([CH:8]([OH:29])[CH:9]([CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([O:22][C:23]([F:27])([F:28])[CH:24]([F:25])[F:26])[CH:17]=2)[C:10]([OH:12])=[O:11])[CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 22261905HCID 22261905, compound

Product 1

HCID 22262162HCID 22262162, compoundYield 74.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of ethyl(2RS,3RS)-3-(6-fluoropyridin-2-yl)-3-hydroxy-2-((3-(1,1,2,2-tetrafluoroethoxy)phenyl)methyl)propionate (5.5 g, 13.1 mmol, (2RS,3RS) form: (2RS,3SR) form=6:1) in methanol (25 ml) was added 2N aqueous sodium hydroxide solution (13.1 ml, 26.2 mmol), and the mixture was stirred at room temperature for 2 hrs. The reaction solution was acidified with 1N hydrochloric acid and extracted with ethyl acetate (200 ml×2). The extract was washed with water and saturated brine, dried over anhydrous magnesium sulfate and evaporated under reduced pressure. Recrystallization of the residue from ethyl acetate-hexane gave (2RS,3RS)-3-(6-fluoropyridin-2-yl)-3-hydroxy-2-((3-(1,1,2,2-tetrafluoroethoxy)phenyl)methyl)propionic acid (3.82 g, 74%).

Workup

  1. extractionextracted with ethyl acetate (200 ml×2)
  2. washThe extract was washed with water and saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customevaporated under reduced pressure
  5. customRecrystallization of the residue from ethyl acetate-hexane

Sources & evidence

ORD record
ord-4993d3dd668442049bf7d91610fdfaf2
Source dataset
uspto-grants-2006_01
Patent number
US06982348B2

Reaction notes

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