Hydrochloric Acid → HCID 22261633, compound

HRID 1610282Notes

Reaction equation

HRID 1610282 reaction equation
[F:1][C:2]1[CH:23]=[CH:22][C:5]([CH2:6][CH:7]([CH:13]([C:15]2[CH:20]=[CH:19][C:18]([F:21])=[CH:17][CH:16]=2)[OH:14])[C:8]([O:10]CC)=[O:9])=[CH:4][CH:3]=1.[OH-].[Na+].Cl>CO>[F:21][C:18]1[CH:19]=[CH:20][C:15]([CH:13]([OH:14])[CH:7]([CH2:6][C:5]2[CH:4]=[CH:3][C:2]([F:1])=[CH:23][CH:22]=2)[C:8]([OH:10])=[O:9])=[CH:16][CH:17]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 86593224HCID 86593224, compound

Product 1

HCID 22261633HCID 22261633, compoundYield 94.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of ethyl (2RS,3RS)-2-(4-fluorobenzyl)-3-(4-fluorophenyl)-3-hydroxypropionate (16.5 g, 51.5 mmol) in methanol (50 ml) was added 2N aqueous sodium hydroxide solution (51.5 ml, 0.103 mol) and the mixture was stirred at room temperature for 3 hrs. The reaction solution was acidified with 1N hydrochloric acid (130 ml) and extracted with ethyl acetate (200, 100 ml). The extract was washed with water, dried over anhydrous magnesium sulfate and evaporated under reduced pressure. The residue was crystallized from, hexane to give (2RS,3RS)-3-(4-fluorophenyl)-2-(4-fluorobenzyl)-3-hydroxypropionic acid (14.2 g, 94%).

Workup

  1. extractionextracted with ethyl acetate (200, 100 ml)
  2. washThe extract was washed with water
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customevaporated under reduced pressure
  5. customThe residue was crystallized from, hexane

Sources & evidence

ORD record
ord-76acc9f9bf9243ee8215971db42877f3
Source dataset
uspto-grants-2006_01
Patent number
US06982348B2

Reaction notes

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