Trifluoroacetic acid → L-Proline, 1-ethyl-5-oxo-

HRID 2238489Notes

Reaction equation

HRID 2238489 reaction equation
[CH2:1]([N:3]1[C:14](=[O:15])[CH2:13][CH2:12][C@H:4]1[C:5]([O:7]C(C)(C)C)=[O:6])[CH3:2].FC(F)(F)C(O)=O>ClCCl>[CH2:1]([N:3]1[C:14](=[O:15])[CH2:13][CH2:12][C@H:4]1[C:5]([OH:7])=[O:6])[CH3:2]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 674618121,1-Dimethylethyl 1-ethyl-5-oxo-prolinate

Product 1

HCID 18605196L-Proline, 1-ethyl-5-oxo-

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1,1-Dimethylethyl 1-ethyl-5-oxo-prolinate (0.965 g) was dissolved in dichloromethane (˜5 ml) and treated with trifluoroacetic acid (1 ml). The mixture was stirred at room temperature for 1.5 hrs and then evaporated. The resulting material was mostly starting material so a further amount of trifluoroacetic acid (1 ml) and dichloromethane (˜5 ml) was added and the mixture stirred at room temperature for 36 hrs. The mixture was evaporated and then toluene was added to the residue and this was in turn also evaporated. After repeating this process once more, crude 1-ethyl-5-oxo-proline was obtained as a dark yellow oil which was used without additional purification.

Workup

  1. customevaporated
  2. additionwas added
  3. stirringthe mixture stirred at room temperature for 36 hrs
  4. customThe mixture was evaporated
  5. additiontoluene was added to the residue
  6. customalso evaporated

Sources & evidence

ORD record
ord-6e4a8f38404840f19ad809c4b5729ffd
Source dataset
uspto-grants-2010_05
Patent number
US07718693B2

Reaction notes

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