[1-(4-Methoxy-benzyl)-2-oxo-1,2,3,4-tetrahydro-quinolin-3-yl]-acetic acid tert-butyl ester → 2-(2-Oxo-1,2,3,4-tetrahydroquinolin-3-YL)acetic acid

HRID 2105543Notes

Reaction equation

HRID 2105543 reaction equation
C([O:5][C:6](=[O:28])[CH2:7][CH:8]1[CH2:17][C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[N:10](CC2C=CC(OC)=CC=2)[C:9]1=[O:27])(C)(C)C>C(O)(C(F)(F)F)=O>[O:27]=[C:9]1[CH:8]([CH2:7][C:6]([OH:28])=[O:5])[CH2:17][C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[NH:10]1

Participants

3

Reactant 1

HCID 69009889[1-(4-Methoxy-benzyl)-2-oxo-1,2,3,4-tetrahydro-quinolin-3-yl]-acetic acid tert-butyl ester

Product 1

HCID 183329702-(2-Oxo-1,2,3,4-tetrahydroquinolin-3-YL)acetic acidYield 93%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

The [1-(4-methoxy-benzyl)-2-oxo-1,2,3,4-tetrahydro-quinolin-3-yl]-acetic acid tert-butyl ester (3.35 mmol) obtained in the previous step is dissolved in 7 mL of TFA and heated to reflux for 1.5 hours. After removal of the excess TFA under reduced pressure, acid-base extraction gives the crude (2-oxo-1,2,3,4-tetrahydro-quinolin-3-yl)-acetic acid as a yellow solid. Yield: 93%.

Workup

  1. temperatureheated
  2. temperatureto reflux for 1.5 hours
  3. customAfter removal of the excess TFA
  4. extractionunder reduced pressure, acid-base extraction

Sources & evidence

ORD record
ord-4795e3f1857c45b3944996f2eb8c01ba
Source dataset
uspto-grants-2009_08
Patent number
US07579363B2

Reaction notes

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