Trifluoroacetic acid → 2-[3-[(4-Chlorophenyl)methylcarbamoyl]-6-(3-hydroxyprop-1-ynyl)-4-oxo-1-quinolyl]acetic acid

HRID 1067981Notes

Reaction equation

HRID 1067981 reaction equation
[Cl:1][C:2]1[CH:34]=[CH:33][C:5]([CH2:6][NH:7][C:8]([C:10]2[C:19](=[O:20])[C:18]3[C:13](=[CH:14][CH:15]=[C:16]([C:21]#[C:22][CH2:23][OH:24])[CH:17]=3)[N:12]([CH2:25][C:26]([O:28]C(C)(C)C)=[O:27])[CH:11]=2)=[O:9])=[CH:4][CH:3]=1.FC(F)(F)C(O)=O>ClCCl>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:6][NH:7][C:8]([C:10]2[C:19](=[O:20])[C:18]3[C:13](=[CH:14][CH:15]=[C:16]([C:21]#[C:22][CH2:23][OH:24])[CH:17]=3)[N:12]([CH2:25][C:26]([OH:28])=[O:27])[CH:11]=2)=[O:9])=[CH:33][CH:34]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 16073847Tert-butyl 2-[3-[(4-chlorophenyl)methylcarbamoyl]-6-(3-hydroxyprop-1-ynyl)-4-oxo-1-quinolyl]acetate

Product 1

HCID 160738482-[3-[(4-Chlorophenyl)methylcarbamoyl]-6-(3-hydroxyprop-1-ynyl)-4-oxo-1-quinolyl]acetic acidYield 80.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a suspension of tert-butyl 2-[3-{[(4-chlorobenzyl)amino]carbonyl}-6-(3-hydroxy-1-propynyl)-4-oxo-1(4H)quinolinyl]acetate (0.07 g) from Example No. 28 in dichloromethane (1 mL) is added trifluoroacetic acid (1 mL). After 3 hours, the resulting solution is concentrated under reduced pressure. The residue is dissolved in a small amount of dichloromethane:methanol:DMF and slowly added to vigorously stirring 1:1 diethyl ether:pentane. The resulting precipitate is collected filtration to afford 0.05 g of the title compound as a solid.

Workup

  1. concentrationthe resulting solution is concentrated under reduced pressure
  2. dissolutionThe residue is dissolved in a small amount of dichloromethane
  3. additionmethanol:DMF and slowly added
  4. customThe resulting precipitate is collected
  5. filtrationfiltration

Sources & evidence

ORD record
ord-66de466a215248a091e6498e44bd7f50
Source dataset
uspto-grants-2001_06
Patent number
US06248739B1

Reaction notes

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