Water → 2-(5-{[(Tert-butoxy)carbonyl]amino}-2-chlorophenyl)acetic acid

HRID 1383369Notes

Reaction equation

HRID 1383369 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])=[CH:4][C:3]=1[CH2:16][C:17]#N.CC(O)C.[OH-:23].[K+].[OH2:25]>>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])=[CH:4][C:3]=1[CH2:16][C:17]([OH:25])=[O:23]

Participants

5

Reactant 4

HCID 962WaterHCID 3776IsopropanolHCID 14797Potassium HydroxideHCID 22600105(2-Chloro-5-(boc-amino)phenyl)acetonitrile

Product 1

HCID 226000942-(5-{[(Tert-butoxy)carbonyl]amino}-2-chlorophenyl)acetic acidYield 50%

Procedure

To a solution of (2-chloro-5-(Boc-amino)phenyl)acetonitrile (5.2 g; 20 mmol; from step (iii) above) in water:i-PrOH (37 mL; 2:1) was added KOH (5 g; 89 mmol), and the solution was refluxed overnight. The mixture was subsequently concentrated, water:THF (50 mL; 1:1) and Boc2O were added, and the mixture was stirred overnight. The THF was evaporated, the water phase was washed with ether (1×50 mL), made acidic with HCl (dilute) and extracted with EtOAc (3×30 mL). The combined organic layers were washed with water, dried (Na2SO4) and concentrated, yielding 2.8 g (50%) of the sub-title compound.

Workup

  1. temperaturethe solution was refluxed overnight
  2. concentrationThe mixture was subsequently concentrated
  3. additionwater:THF (50 mL; 1:1) and Boc2O were added
  4. customThe THF was evaporated
  5. washthe water phase was washed with ether (1×50 mL)
  6. extractionextracted with EtOAc (3×30 mL)
  7. washThe combined organic layers were washed with water
  8. dry with materialdried (Na2SO4)
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-2e32e7118b344d089f72615b7300dc44
Source dataset
uspto-grants-2001_07
Patent number
US06255301B1

Reaction notes

Loading…