Sodium Hydroxide → HCID 21048467, compound

HRID 1985782Notes

Reaction equation

HRID 1985782 reaction equation
C[O:2][C:3](=[O:25])[C@@H:4]([NH:14][C:15]([O:17][CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)=[O:16])[CH2:5][C:6]1[C:11]([F:12])=[CH:10][CH:9]=[CH:8][C:7]=1[F:13].[OH-].[Na+]>CO>[CH2:18]([O:17][C:15]([NH:14][C@@H:4]([CH2:5][C:6]1[C:7]([F:13])=[CH:8][CH:9]=[CH:10][C:11]=1[F:12])[C:3]([OH:25])=[O:2])=[O:16])[C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 67391680(2S)-benzyloxycarbonylamino-3-(2,6-difluorophenyl)propionic acid methyl ester

Product 1

HCID 21048467HCID 21048467, compoundYield 95.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

2(S)-Benzyloxycarbonylamino-3-(2,6-difluorophenyl)propionic acid methyl ester (5 g, 14.4 mmol) was dissolved in methanol (60 mL) and cooled on ice. 1 N NaOH (22 mL, 22 mmol) was added dropwise over 15 min. The reaction mixture was removed from cooling bath and stirring was continued at room temperature for 4 h. The solvent was then removed by rotary evaporation and the residue was treated with water (100 mL) and then with 1 N HCl to adjust the pH to 4. The product was extracted with ethyl acetate (300 mL, 200 mL). Evaporation of the solvent and crystallization of the residue from methylene chloride/hexane gave 2(S)-benzyloxycarbonylamino-3-(2,6-difluorophenyl)propionic acid (4.6 g, 13.7 mmol, 94% yield).

Workup

  1. temperaturecooled on ice
  2. customThe reaction mixture was removed
  3. temperaturefrom cooling bath
  4. customThe solvent was then removed by rotary evaporation
  5. additionthe residue was treated with water (100 mL)
  6. extractionThe product was extracted with ethyl acetate (300 mL, 200 mL)
  7. customEvaporation of the solvent and crystallization of the residue from methylene chloride/hexane

Sources & evidence

ORD record
ord-9b6cc5acbd7e48479aa84f72d8b5204f
Source dataset
uspto-grants-2009_06
Patent number
US07547701B2

Reaction notes

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