Trifluoroacetic acid → Phthalylglycine aldehyde

HRID 861367Notes

Reaction equation

HRID 861367 reaction equation
C([O:3][CH:4](OCC)[CH2:5][N:6]1[C:10](=[O:11])[C:9]2=[CH:12][CH:13]=[CH:14][CH:15]=[C:8]2[C:7]1=[O:16])C.FC(F)(F)C(O)=O>C1(C)C=CC=CC=1>[C:7]1(=[O:16])[N:6]([CH2:5][CH:4]=[O:3])[C:10](=[O:11])[C:9]2=[CH:12][CH:13]=[CH:14][CH:15]=[C:8]12

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 3152862-Phthalimidoacetaldehyde Diethyl Acetal

Product 1

HCID 76201Phthalylglycine aldehydeYield 83.5%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of 50.0 g (190 mmol) of 2-(phthalimido)acetaldehyde diethyl acetal in 300 mL of toluene was treated with 150 mL of 50% aqueous trifluoroacetic acid and the mixture was stirred vigorously at ambient temperature for 72 h. The solution was concentrated in vacuo and 100 mL of ethyl acetate was added. The white precipitate was filtered off and washed with ice-cold ethyl acetate (100 mL) to give 30.0 g (78%) of the title compound.

Workup

  1. concentrationThe solution was concentrated in vacuo and 100 mL of ethyl acetate
  2. additionwas added
  3. filtrationThe white precipitate was filtered off
  4. washwashed with ice-cold ethyl acetate (100 mL)

Sources & evidence

ORD record
ord-8aa61391c32449c281f45d3595d52de7
Source dataset
uspto-grants-1998_02
Patent number
US05714487

Reaction notes

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