HCID 22405068, compound → HCID 22405038, compound

HRID 441247Notes

Reaction equation

HRID 441247 reaction equation
C([O:5][C:6]([CH2:8][N:9]1[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[N:12]([C:19](=[O:42])[C:20]2[CH:25]=[CH:24][C:23]([NH:26][C:27](=[O:41])[C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=3[C:34]3[CH:39]=[CH:38][C:37]([CH3:40])=[CH:36][CH:35]=3)=[CH:22][CH:21]=2)[CH2:11][C:10]1=[O:43])=[O:7])(C)(C)C>FC(F)(F)C(O)=O>[C:6]([CH2:8][N:9]1[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[N:12]([C:19](=[O:42])[C:20]2[CH:21]=[CH:22][C:23]([NH:26][C:27](=[O:41])[C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=3[C:34]3[CH:35]=[CH:36][C:37]([CH3:40])=[CH:38][CH:39]=3)=[CH:24][CH:25]=2)[CH2:11][C:10]1=[O:43])([OH:7])=[O:5]

Participants

3

Reactant 1

HCID 22405068HCID 22405068, compound

Product 1

HCID 22405038HCID 22405038, compoundYield 84.7%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

A solution of 1-(t-Butoxycarbonylmethyl)-4-{4-[2-(4methylphenyl)benzoylamino]benzoyl}-1,2,3,4-tetrahydroquinoxalin -2-one (370 mg) in aqueous trifluoroacetic acid (15 ml) was stirred at ambient temperature for 2 hours and the solvent was evaporated in vacuo. The residue was dissolved in chloroform and the solution was washed with water and brine, and dried over magnesium sulfate. The solvent was evaporated in vacuo and the residue was purified by silica gel column (2% methanol in chloroform). The solvent was evaporated in vacuo and the residue was solidified with diethyl ether to give 1-carboxymethyl 4-{4-[2-(4-methylphenyl)benzoylamino]benzoyl}-1,2,3,4-tetrahydroquinoxalin-2-one (283 mg) as a white powder.

Workup

  1. customthe solvent was evaporated in vacuo
  2. dissolutionThe residue was dissolved in chloroform
  3. washthe solution was washed with water and brine
  4. dry with materialdried over magnesium sulfate
  5. customThe solvent was evaporated in vacuo
  6. customthe residue was purified by silica gel column (2% methanol in chloroform)
  7. customThe solvent was evaporated in vacuo

Sources & evidence

ORD record
ord-fbd27b452512488f84122b9c3703af60
Source dataset
uspto-grants-1996_05
Patent number
US05521170

Reaction notes

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