Oxalic Acid → HCID 69458827, compound

HRID 1351984Notes

Reaction equation

HRID 1351984 reaction equation
[CH3:1][C@@H:2]([NH:24]C(=O)OC(C)(C)C)[CH2:3][C:4]1[C:12]2[C:7](=[C:8]([O:13][C@@H:14]([CH3:23])[C:15]([N:17]3[CH2:22][CH2:21][O:20][CH2:19][CH2:18]3)=[O:16])[CH:9]=[CH:10][CH:11]=2)[NH:6][CH:5]=1.C(O)(=O)C(O)=O>C(#N)C>[CH3:1][C@@H:2]([NH2:24])[CH2:3][C:4]1[C:12]2[C:7](=[C:8]([O:13][C@@H:14]([CH3:23])[C:15]([N:17]3[CH2:22][CH2:21][O:20][CH2:19][CH2:18]3)=[O:16])[CH:9]=[CH:10][CH:11]=2)[NH:6][CH:5]=1

Participants

4

Reactant 2

HCID 971Oxalic AcidHCID 86604033HCID 86604033, compound

Product 1

HCID 69458827HCID 69458827, compoundYield 79%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of tert-butyl (1R)-1-methyl-2-(7-{[(1S)-1-methyl-2-morpholin-4-yl-2-oxoethyl]oxy}-1H-indol-3-yl)ethylcarbamate (1.03 g, 2.39 mmol) in acetonitrile (10 mL) is added oxalic acid (860 mg, 9.55 mmol), and the mixture is refluxed for 5 hours. The reaction solution is evaporated under reduced pressure to remove the solvent, and to the residue are added a 10% aqueous potassium carbonate solution and a mixture of chloroform:methanol (10:1) for separation. The organic layer is dried over anhydrous potassium carbonate, and the solvent is removed by distillation to give the title compound (626 mg, yield: 79%).

Workup

  1. temperaturethe mixture is refluxed for 5 hours
  2. customThe reaction solution is evaporated under reduced pressure
  3. customto remove the solvent
  4. additionto the residue are added a 10% aqueous potassium carbonate solution
  5. additiona mixture of chloroform:methanol (10:1)
  6. customfor separation
  7. dry with materialThe organic layer is dried over anhydrous potassium carbonate
  8. customthe solvent is removed by distillation

Sources & evidence

ORD record
ord-3ba69ca105bd416db59dade67bf9bb3e
Source dataset
uspto-grants-2007_05
Patent number
US07217724B2

Reaction notes

Loading…