Trifluoroacetic acid → HCID 67458673, compound

HRID 554150Notes

Reaction equation

HRID 554150 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-a0920dbf98e0426387223f42b564fd85
Source dataset
uspto-grants-2011_11
Patent number
US08048907B2

Reaction notes

Loading…