Sodium Hydroxide → 2(S)-(N,N-dibenzylamino)-3-cyclohexylpropionic acid

HRID 259831Notes

Reaction equation

HRID 259831 reaction equation
[CH2:1]([N:8]([C@@H:16]([CH2:21][CH:22]1[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]1)[C:17]([O:19]C)=[O:18])[CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[Na+]>CO>[CH2:1]([N:8]([C@@H:16]([CH2:21][CH:22]1[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]1)[C:17]([OH:19])=[O:18])[CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 22861690methyl 2(S)-(N,N-dibenzylamino)-3-cyclohexylpropionate

Product 1

HCID 156220192(S)-(N,N-dibenzylamino)-3-cyclohexylpropionic acidYield 99.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Methyl 2(S)-(N,N-dibenzylamino)-3-cyclohexylpropionate (200 g) was dissolved in methanol (1 l), and thereto was added an aqueous solution of sodium hydroxide (sodium hydroxide 32.8 g, water 200 ml), followed by refluxing for 6 hours. After the completion of the reaction, the reaction mixture was concentrated, and ethyl acetate (1 l) was added to the residue for dissolution, after which water (400 ml) was added for partition. The organic layer was separated, washed with an aqueous solution of 10% citric acid (400 ml) and saturated brine (400 ml), and dried over magnesium sulfate. The solvent was evaporated under reduced pressure to give 191.1 g of 2(S)-(N,N-dibenzylamino)-3-cyclohexylpropionic acid.

Workup

  1. temperatureby refluxing for 6 hours
  2. customAfter the completion of the reaction
  3. concentrationthe reaction mixture was concentrated
  4. additionethyl acetate (1 l) was added to the residue for dissolution
  5. additionafter which water (400 ml) was added
  6. customfor partition
  7. customThe organic layer was separated
  8. washwashed with an aqueous solution of 10% citric acid (400 ml) and saturated brine (400 ml)
  9. dry with materialdried over magnesium sulfate
  10. customThe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-aee399b8691b4224bae3fcaed736f6fb
Source dataset
uspto-grants-1996_06
Patent number
US05523410

Reaction notes

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