Sodium Hydroxide → (2RS,3RS)-2-(4-tert-butoxybenzyl)-3-(3-chlorophenyl)-3-hydroxypropanoic acid

HRID 1610632Notes

Reaction equation

HRID 1610632 reaction equation
[C:1]([O:5][C:6]1[CH:27]=[CH:26][C:9]([CH2:10][CH:11]([CH:17]([C:19]2[CH:24]=[CH:23][CH:22]=[C:21]([Cl:25])[CH:20]=2)[OH:18])[C:12]([O:14]CC)=[O:13])=[CH:8][CH:7]=1)([CH3:4])([CH3:3])[CH3:2].[OH-].[Na+]>CO>[C:1]([O:5][C:6]1[CH:27]=[CH:26][C:9]([CH2:10][CH:11]([CH:17]([C:19]2[CH:24]=[CH:23][CH:22]=[C:21]([Cl:25])[CH:20]=2)[OH:18])[C:12]([OH:14])=[O:13])=[CH:8][CH:7]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 86593282ethyl (2RS,3RS)-2-(4-tert-butoxybenzyl)-3-(3-chlorophenyl)-3-hydroxypropanoate

Product 1

HCID 22261916(2RS,3RS)-2-(4-tert-butoxybenzyl)-3-(3-chlorophenyl)-3-hydroxypropanoic acid

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of ethyl (2RS,3RS)-2-(4-tert-butoxybenzyl)-3-(3-chlorophenyl)-3-hydroxypropanoate (7.12 g, 18.2 mmol) in methanol (60 ml) was added 2N aqueous sodium hydroxide solution (18.2 ml, 36.4 mmol), and the mixture was stirred overnight at room temperature. The reaction solution was concentrated and acidified with 1N hydrochloric acid. The mixture was extracted with ethyl acetate (200 ml×2). The extract was washed with water and saturated brine, dried (anhydrous magnesium sulfate) and evaporated under reduced pressure. The residue was recrystallized from ethyl acetate-hexane to give the objective substance (4.70 g, 82%).

Workup

  1. concentrationThe reaction solution was concentrated
  2. extractionThe mixture was extracted with ethyl acetate (200 ml×2)
  3. washThe extract was washed with water and saturated brine
  4. dry with materialdried (anhydrous magnesium sulfate)
  5. customevaporated under reduced pressure
  6. customThe residue was recrystallized from ethyl acetate-hexane
  7. customto give the objective substance (4.70 g, 82%)

Sources & evidence

ORD record
ord-c917ef70da7149f28383e26959d2bdbe
Source dataset
uspto-grants-2006_01
Patent number
US06982348B2

Reaction notes

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