Trifluoroacetic acid → Phthalylglycine aldehyde

HRID 1594594Notes

Reaction equation

HRID 1594594 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 hours. 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-d65e7150a4a74078a6e061a2ceeb5a22
Source dataset
uspto-grants-2001_09
Patent number
US06284757B1

Reaction notes

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