Trifluoroacetic acid → HCID 67458673, compound

HRID 2238556Notes

Reaction equation

HRID 2238556 reaction equation
[CH3:1][N:2]1[C:13](=[O:14])[CH2:12][CH:11]([CH3:15])[C@H:3]1[C:4]([O:6]C(C)(C)C)=[O:5].FC(F)(F)C(O)=O>ClCCl>[CH3:1][N:2]1[C:13](=[O:14])[CH2:12][CH:11]([CH3:15])[C@H:3]1[C:4]([OH:6])=[O:5]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acid2×HCID 67461073HCID 67461073, compound

Product 1

HCID 67458673HCID 67458673, compoundYield 133.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

1,1-Dimethylethyl 1,3-dimethyl-5-oxoprolinate (0.770 g, 3.62 mmol) was suspended in dichloromethane (5 ml) and treated with trifluoroacetic acid (0.4 ml, 5.4 mmol). The mixture was stirred for 5 hrs and then evaporated. Azeotroping the resulting residue with toluene then gave unreacted starting material (0.600 g). This was again taken up in dichloromethane (2 ml) and treated with trifluoroacetic acid (2 ml) once more. After stirring for 2 hrs the mixture was evaporated and the residue again azeotroped with toluene (10 ml) to give crude 1,3-dimethyl-5-oxoproline (0.760 g) which was used without any additional purification.

Workup

  1. customevaporated
  2. customAzeotroping the resulting residue with toluene
  3. customthen gave unreacted
  4. stirringAfter stirring for 2 hrs the mixture
  5. customwas evaporated
  6. customthe residue again azeotroped with toluene (10 ml)

Sources & evidence

ORD record
ord-f7ec1c14fbe94f4a87816657a40aacd9
Source dataset
uspto-grants-2010_05
Patent number
US07718693B2

Reaction notes

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