Sodium Hydroxide → (2R)-4-((4-chlorophenyl)amino)-2-cyclohexyl-4-oxobutanoic acid

HRID 1162291Notes

Reaction equation

HRID 1162291 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9](=[O:22])[CH2:10][C@H:11]([CH:16]2[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]2)[C:12]([O:14]C)=[O:13])=[CH:4][CH:3]=1.[OH-].[Na+]>CO.C1COCC1>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([NH:8][C:9](=[O:22])[CH2:10][C@H:11]([CH:16]2[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]2)[C:12]([OH:14])=[O:13])=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 68647026methyl(2R)-4-((4-chlorophenyl)amino)-2-cyclohexyl-4-oxobutanoate

Product 1

HCID 68647359(2R)-4-((4-chlorophenyl)amino)-2-cyclohexyl-4-oxobutanoic acidYield 100.9%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

Methyl(2R)-4-((4-chlorophenyl)amino)-2-cyclohexyl-4-oxobutanoate (0.29 g) obtained in Example 5a) and 1 N sodium hydroxide (1.0 ml) were dissolved in methanol (12 ml) and THF (3 ml), and mixed at room temperature for 1 hour. Then, the reaction solution was concentrated under reduced pressure, acidified by adding 1 N hydrochloric acid to the concentrated solution and extracted with ethyl acetate. The extract was dried over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure to obtain the title compound as pale brown powder (0.28 g, quantitative).

Workup

  1. concentrationThen, the reaction solution was concentrated under reduced pressure
  2. additionby adding 1 N hydrochloric acid to the concentrated solution
  3. extractionextracted with ethyl acetate
  4. dry with materialThe extract was dried over anhydrous sodium sulfate
  5. distillationthe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-4f0face82d934771a735ae13dd1bb630
Source dataset
uspto-grants-2010_10
Patent number
US07820673B2

Reaction notes

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