Trifluoroacetic acid → HCID 86749475, compound

HRID 439613Notes

Reaction equation

HRID 439613 reaction equation
C([O:5][C:6]([CH2:8][N:9]1[C:13](=[O:14])/[C:12](=[CH:15]/[C:16]2[CH:21]=[C:20]([O:22][CH3:23])[C:19]([O:24][CH3:25])=[C:18]([O:26][CH3:27])[CH:17]=2)/[C:11](=[CH:28]\[C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)/[C:10]1=[O:35])=[O:7])(C)(C)C.FC(F)(F)C(O)=O>ClCCl>[C:6]([CH2:8][N:9]1[C:13](=[O:14])/[C:12](=[CH:15]/[C:16]2[CH:21]=[C:20]([O:22][CH3:23])[C:19]([O:24][CH3:25])=[C:18]([O:26][CH3:27])[CH:17]=2)/[C:11](=[CH:28]\[C:29]2[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=2)/[C:10]1=[O:35])([OH:7])=[O:5]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86749476HCID 86749476, compound

Product 1

HCID 86749475HCID 86749475, compoundYield 81%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (3E,4E)-1-t-butoxycarbonylmethyl-3-benzylidene-4-(3,4,5-trimethoxybenzylidene)-2,5-pyrrolidinedione (3.5 g) obtained in Example 42 in dichloromethane (40 ml) is added trifluoroacetic acid (10 ml) at room temperature, and the mixture is allowed to stand for 4 hours. The mixture is evaporated under reduced pressure to remove the solvent, and to the residue is added trichloromethane. The mixture is washed, dried, and evaporated to remove the solvent. The resulting residue is crystallized from diethyl ether to give (3E,4E)-1-carboxymethyl-3-benzylidene-4-(3,4,5-trimethoxybenzylidene)-2,5-pyrrolidinedione (2.5 g) as yellow prisms.

Workup

  1. customThe mixture is evaporated under reduced pressure
  2. customto remove the solvent
  3. additionto the residue is added trichloromethane
  4. washThe mixture is washed
  5. customdried
  6. customevaporated
  7. customto remove the solvent
  8. customThe resulting residue is crystallized from diethyl ether

Sources & evidence

ORD record
ord-2d8eee9ff3304f4db1a716624acab3aa
Source dataset
uspto-grants-1996_05
Patent number
US05514815

Reaction notes

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