Ethyl Acetate → HCID 136385127, compound

HRID 1986483Notes

Reaction equation

HRID 1986483 reaction equation
[NH2:1]/[C:2](=[N:33]\[OH:34])/[C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[N:9]=[C:8]([CH2:13][CH:14]([CH3:16])[CH3:15])[C:7]([CH2:17][NH:18][C:19](=[O:25])[O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[C:6]2[C:26]1[CH:31]=[CH:30][C:29]([CH3:32])=[CH:28][CH:27]=1.[C:35](OCC)(=[O:37])C.C1N=CN(C(N2C=NC=C2)=O)C=1>O1CCCC1>[CH2:13]([C:8]1[C:7]([CH2:17][NH:18][C:19](=[O:25])[O:20][C:21]([CH3:22])([CH3:23])[CH3:24])=[C:6]([C:26]2[CH:27]=[CH:28][C:29]([CH3:32])=[CH:30][CH:31]=2)[C:5]2[C:10](=[CH:11][CH:12]=[C:3]([C:2]3[NH:1][C:35](=[O:37])[O:34][N:33]=3)[CH:4]=2)[N:9]=1)[CH:14]([CH3:16])[CH3:15]

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 682631,1'-CarbonyldiimidazoleHCID 172982812HCID 172982812, compound

Product 1

HCID 136385127HCID 136385127, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of tert-butyl [6-[(Z)-amino(hydroxyimino)methyl]-2-isobutyl-4-(4-methylphenyl)quinolin-3-yl]methylcarbamate (0.25 g, 0.54 mmol) in tetrahydrofuran (10 ml)-ethyl acetate (10 ml) was added N,N-carbonyldiimidazole (0.26 g, 1.6 mmol), and the mixture was heated under reflux for 3 hrs. The reaction mixture was partitioned between ethyl acetate and 0.1M aqueous citric acid solution. The organic layer was washed with saturated brine and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure and the residue was crystallized from n-hexane-ethyl acetate to give tert-butyl [2-isobutyl-4-(4-methylphenyl)-6-(5-oxo-4,5-dihydro-1,2,4-oxadiazol-3-yl)quinolin-3-yl]methylcarbamate (0.24 g, yield 90%) as a white powder.

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 3 hrs
  3. customThe reaction mixture was partitioned between ethyl acetate and 0.1M aqueous citric acid solution
  4. washThe organic layer was washed with saturated brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customThe solvent was evaporated under reduced pressure
  7. customthe residue was crystallized from n-hexane-ethyl acetate

Sources & evidence

ORD record
ord-2a255f1584ef4affb113a64fffe5ba5c
Source dataset
uspto-grants-2009_06
Patent number
US07547710B2

Reaction notes

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