Sodium Hydroxide → HCID 12043847, compound

HRID 2227514Notes

Reaction equation

HRID 2227514 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([CH2:7][NH:8][C:9](/[CH:11]=[CH:12]/[C:13]2[CH:18]=[CH:17][C:16]([N:19]([CH2:26][C:27]([O:29]C(C)(C)C)=[O:28])C(=O)C(F)(F)F)=[CH:15][CH:14]=2)=[O:10])[CH:2]=1.[OH-].[Na+]>CO>[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([CH2:7][NH:8][C:9](/[CH:11]=[CH:12]/[C:13]2[CH:14]=[CH:15][C:16]([NH:19][CH2:26][C:27]([OH:29])=[O:28])=[CH:17][CH:18]=2)=[O:10])[CH:2]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 86758308HCID 86758308, compound

Product 1

HCID 12043847HCID 12043847, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
60 °C

Procedure

A solution of t-butyl [[4-[(E)-2-[N-(3-pyridylmethyl)carbamoyl]ethenyl]-phenyl](trifluoroacetyl)amino]acetate (580 mg) in aqueous methanol was mixed with 74 mg of sodium hydroxide, and then stirred at room temperature for 24 hours and subsequently at 60° C. for 1 hour. After evaporation of methanol, the reaction mixture was mixed with 0.4 ml of 2 mol/l hydrochloric acid, and extracted with ethyl acetate. The organic layer was dried over sodium sulfate. The drying agent was filtered off and the solvent was evaporated to precipitate a solid, which was then washed with methanol/ethyl acetate and dried by heating under reduced pressure to provide [[4-[(E)-2-[N-(3-pyridylmethyl)carbamoyl]ethenyl]phenyl]amino]acetic acid of interest (78 mg, 20%) as a pale yellow solid.

Workup

  1. customAfter evaporation of methanol
  2. additionthe reaction mixture was mixed with 0.4 ml of 2 mol/l hydrochloric acid
  3. extractionextracted with ethyl acetate
  4. dry with materialThe organic layer was dried over sodium sulfate
  5. filtrationThe drying agent was filtered off
  6. customthe solvent was evaporated
  7. customto precipitate a solid, which
  8. washwas then washed with methanol/ethyl acetate
  9. customdried
  10. temperatureby heating under reduced pressure

Sources & evidence

ORD record
ord-9edaf9e759994989a9858eca33a2b416
Source dataset
uspto-grants-2002_07
Patent number
US06413995B1

Reaction notes

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