Sodium Hydroxide → HCID 22261843, compound

HRID 1610625Notes

Reaction equation

HRID 1610625 reaction equation
[C:1]([C:5]1[CH:26]=[CH:25][C:8]([CH2:9][CH:10]([CH:16]([C:18]2[CH:23]=[CH:22][CH:21]=[C:20]([Cl:24])[CH:19]=2)[OH:17])[C:11]([O:13]CC)=[O:12])=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].[OH-].[Na+]>C(O)C>[C:1]([C:5]1[CH:26]=[CH:25][C:8]([CH2:9][CH:10]([CH:16]([C:18]2[CH:23]=[CH:22][CH:21]=[C:20]([Cl:24])[CH:19]=2)[OH:17])[C:11]([OH:13])=[O:12])=[CH:7][CH:6]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 86593281HCID 86593281, compound

Product 1

HCID 22261843HCID 22261843, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of ethyl (2RS,3RS)-2-(4-tert-butylbenzyl)-3-(3-chlorophenyl)-3-hydroxypropanoate (26.5 g, 70.7 mmol) in ethanol (200 ml) was added 2N aqueous sodium hydroxide solution (70 ml, 140 mmol), and the mixture was stirred overnight at room temperature. The reaction solution was concentrated, acidified with 1N hydrochloric acid and extracted with ethyl acetate (500 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 (15.0 g, 59%).

Workup

  1. concentrationThe reaction solution was concentrated
  2. extractionextracted with ethyl acetate (500 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 (15.0 g, 59%)

Sources & evidence

ORD record
ord-fe8e47e4ec6c401fbffcc702582e9f23
Source dataset
uspto-grants-2006_01
Patent number
US06982348B2

Reaction notes

Loading…