Sodium Hydroxide → HCID 54152681, compound

HRID 1379184Notes

Reaction equation

HRID 1379184 reaction equation
[C:1]([O:5][C:6]([N:8]([C@@H:16]([CH2:27][C:28]1[CH:37]=[CH:36][C:35]2[C:30](=[CH:31][CH:32]=[CH:33][CH:34]=2)[CH:29]=1)[C:17]([O:19]CC1C=CC=CC=1)=[O:18])[CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[OH-].[Na+]>CO>[CH2:9]([N:8]([C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:7])[C@H:16]([C:17]([OH:19])=[O:18])[CH2:27][C:28]1[CH:37]=[CH:36][C:35]2[C:30](=[CH:31][CH:32]=[CH:33][CH:34]=2)[CH:29]=1)[C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 86751288HCID 86751288, compound

Product 1

HCID 54152681HCID 54152681, compoundYield 34.9%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Benzyl (2S)-2-[N-(tert-butoxycarbonyl)-N-benzylamino]-3-(2-naphthyl)propionate (10.5 g) was dissolved in methanol (100 ml) and aqueous 1N sodium hydroxide solution (20 ml) was added at ice-bath temperature. The mixture was stirred at room temperature overnight. The reaction mixture was poured into ice-water and extracted with diisopropyl ether. The aqueous layer was adjusted to pH 3 by adding dilute hydrochloric acid and extracted with ethyl acetate. The extract was washed with brine and dried over magnesium sulfate. Evaporation of the solvent gave N-benzyl-N-(tert-butoxycarbonyl)-3-(2-naphthyl)-L-alanine (3.0 g).

Workup

  1. extractionextracted with diisopropyl ether
  2. additionby adding dilute hydrochloric acid
  3. extractionextracted with ethyl acetate
  4. washThe extract was washed with brine
  5. dry with materialdried over magnesium sulfate
  6. customEvaporation of the solvent

Sources & evidence

ORD record
ord-884f0c2db99b416cb3fc1f38a9986956
Source dataset
uspto-grants-1997_09
Patent number
US05670505

Reaction notes

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