Trifluoroacetic acid → (S)-1-(3-chloro-5-trifluoromethyl-pyridin-2-yl)-5-oxo-pyrrolidine-2-carboxylic acid

HRID 469734Notes

Reaction equation

HRID 469734 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[C:19]([Cl:20])=[CH:18][C:17]([C:21]([F:24])([F:23])[F:22])=[CH:16][N:15]=1)=[O:7])(C)(C)C.FC(F)(F)C(O)=O>>[Cl:20][C:19]1[C:14]([N:9]2[C:10](=[O:13])[CH2:11][CH2:12][C@H:8]2[C:6]([OH:7])=[O:5])=[N:15][CH:16]=[C:17]([C:21]([F:23])([F:22])[F:24])[CH:18]=1

Participants

3

Reactant 2

HCID 6422Trifluoroacetic acidHCID 67455590(S)-1-(3-chloro-5-trifluoromethyl-pyridin-2-yl)-5-oxo-pyrrolidine-2-carboxylic acid tert-butyl ester

Product 1

HCID 67455316(S)-1-(3-chloro-5-trifluoromethyl-pyridin-2-yl)-5-oxo-pyrrolidine-2-carboxylic acid

Procedure

(S)-1-(3-Chloro-5-trifluoromethyl-pyridin-2-yl)-5-oxo-pyrrolidine-2-carboxylic acid tert-butyl ester (760 mg, 2.1 mmol) is treated with pre-cooled trifluoroacetic acid (5 mL). The clear solution is kept at room temperature for 1 h. Trifluoroacetic acid is evaporated in vacuo and the concentrate is treated with ice/water. Precipitated white solid is filtered, washed with water to give the title compound, ESI m/z 309 [M+H]+.

Workup

  1. customTrifluoroacetic acid is evaporated in vacuo
  2. additionthe concentrate is treated with ice/water
  3. customPrecipitated white solid
  4. filtrationis filtered
  5. washwashed with water

Sources & evidence

ORD record
ord-538f9bd7099e4d7b932ff407e769f0e3
Source dataset
uspto-grants-2014_01
Patent number
US08629157B2

Reaction notes

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