Trifluoroacetic acid → HCID 20194623, compound

HRID 653416Notes

Reaction equation

HRID 653416 reaction equation
C([O:5][C:6](=[O:16])[CH2:7][CH2:8][CH:9]1[CH2:13][CH:12]([OH:14])[C:11](=[O:15])[NH:10]1)(C)(C)C.FC(F)(F)C(O)=O>CN(C)C=O>[OH:14][CH:12]1[C:11](=[O:15])[NH:10][CH:9]([CH2:8][CH2:7][C:6]([OH:16])=[O:5])[CH2:13]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 13911556HCID 13911556, compound

Product 1

HCID 20194623HCID 20194623, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

4-Hydroxy-5-oxo-2-pyrrolidinepropanoic acid t-butyl ester (1.87 g) and trifluoroacetic acid (1.2 g) in 10 ml of N,N-dimethylformamide was heated at 100° C. until disappearance of starting material by thin layer chromatography. After concentration under reduced pressure, the resulting solid is washed with acetone and filtered to give 4-hydroxy-5-oxo-2-pyrrolidinepropanoic acid. NMR (DMSOD6) and 12.14 (s, 1H), 7.96 (d, J=5 Hz, 1H), 5.37 (m, 1H), 4.00 (m, 1H), 2.60-1.09 (m, 6H). IR (cm-1) 3420, 3080, 2030, 2920, 1698, 1494, 1387, 1284.

Workup

  1. concentrationAfter concentration under reduced pressure
  2. washthe resulting solid is washed with acetone
  3. filtrationfiltered

Sources & evidence

ORD record
ord-5e2f5bb5eaeb45cc9d60143024526f2d
Source dataset
uspto-grants-1987_06
Patent number
US04677114

Reaction notes

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