Dichloromethane → HCID 67634869, compound

HRID 1075675Notes

Reaction equation

HRID 1075675 reaction equation
[CH3:1][O:2][C:3](=[O:39])[C@H:4]([CH3:38])[NH:5][C:6](=[O:37])[CH2:7][N:8]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[C:10](=[CH:17][C:18]2[CH:27]=[CH:26][C:25]([O:28]CC3C=CC=CC=3)=[C:24]3[C:19]=2[CH:20]=[CH:21][CH:22]=[N:23]3)[C:9]1=[O:36].FC(F)(F)S(O)(=O)=O.ClCCl.C([O-])(O)=O.[Na+]>FC(F)(F)C(O)=O>[CH3:1][O:2][C:3](=[O:39])[C@H:4]([CH3:38])[NH:5][C:6](=[O:37])[CH2:7][N:8]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[C:10](=[CH:17][C:18]2[CH:27]=[CH:26][C:25]([OH:28])=[C:24]3[C:19]=2[CH:20]=[CH:21][CH:22]=[N:23]3)[C:9]1=[O:36]

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 62406Trifluoromethanesulfonic acidHCID 516892Sodium BicarbonateHCID 67619232HCID 67619232, compound

Product 1

HCID 67634869HCID 67634869, compoundYield 77.3%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Conditions

Temperature
2.5 °C

Procedure

To a solution of N-{2-[3-(8-benzyloxyquinol-5-ylmethylen)-2-oxindol-1-yl]acetyl}alanine methyl ester (45 mg, 0.09 mmol) in trifluoroacetic acid (5 ml) was added trifluoromethanesulfonic acid (0.1 ml) and the mixture was stirred at 0-5° C. for 0.5 h. Then dichloromethane was added, the mixture neutralized with 5% NaHCO3 and the organic layer concentrated under vacuum to give 30 mg of title compound (77% yield).

Workup

  1. concentrationthe organic layer concentrated under vacuum

Sources & evidence

ORD record
ord-58fee70a9f42411b9efbfc9d96f72005
Source dataset
uspto-grants-1999_05
Patent number
US05905149

Reaction notes

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