Trifluoroacetic acid → (S)-1-(4-nitro-phenyl)-5-oxo-pyrrolidine-2-carboxylic acid

HRID 469729Notes

Reaction equation

HRID 469729 reaction equation
C([O:5][C:6]([C@@H:8]1[CH2:12][CH2:11][C:10](=[O:13])[N:9]1[C:14]1[CH:19]=[CH:18][C:17]([N+:20]([O-:22])=[O:21])=[CH:16][CH:15]=1)=[O:7])(C)(C)C.FC(F)(F)C(O)=O>>[N+:20]([C:17]1[CH:16]=[CH:15][C:14]([N:9]2[C:10](=[O:13])[CH2:11][CH2:12][C@H:8]2[C:6]([OH:7])=[O:5])=[CH:19][CH:18]=1)([O-:22])=[O:21]

Participants

3

Reactant 2

HCID 6422Trifluoroacetic acidHCID 67456456(S)-1-(4-nitro-phenyl)-5-oxo-pyrrolidine-2-carboxylic acid tert-butyl ester

Product 1

HCID 67457654(S)-1-(4-nitro-phenyl)-5-oxo-pyrrolidine-2-carboxylic acid

Procedure

(S)-1-(4-nitro-phenyl)-5-oxo-pyrrolidine-2-carboxylic acid tert-butyl ester (800 mg, 2.6 mmol) is treated with trifluoroacetic acid (5 mL) at room temperature. After 1 h trifluoroacetic acid is evaporated in vacuo and the concentrate treated with ice/water. Precipitated light brownish solid is filtered washed with water and dried to give the title compound, ESI m/z 251 [M+H]+.

Workup

  1. customAfter 1 h trifluoroacetic acid is evaporated in vacuo
  2. additionthe concentrate treated with ice/water
  3. customPrecipitated light brownish solid
  4. filtrationis filtered
  5. washwashed with water
  6. customdried

Sources & evidence

ORD record
ord-009fdd8764b44a0cb60343e9b8c40ac3
Source dataset
uspto-grants-2014_01
Patent number
US08629157B2

Reaction notes

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