Ammonia → HCID 19596580, compound

HRID 612874Notes

Reaction equation

HRID 612874 reaction equation
[C:1]([O:5][C:6]([NH:8][CH2:9][CH2:10][O:11][C:12]1[C:16]([C:17](O)=[O:18])=[C:15]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[O:14][N:13]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C(N1C=CN=C1)([N:28]1C=CN=C1)=O.N>O1CCCC1>[C:1]([O:5][C:6]([NH:8][CH2:9][CH2:10][O:11][C:12]1[C:16]([C:17](=[O:18])[NH2:28])=[C:15]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[O:14][N:13]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 222AmmoniaHCID 682631,1'-CarbonyldiimidazoleHCID 19596598HCID 19596598, compound

Product 1

HCID 19596580HCID 19596580, compoundYield 100.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

3-(2-(N-tert-Butoxycarbonylamino)ethoxy)-4-carboxy-5-phenylisoxazole (0.6 g) was dissolved in tetrahydrofuran (6 ml) and carbonyldiimidazole (0.31 g) was added thereto under ice-cooling with stirring, followed by stirring of the mixture at room temperature for 30 minutes. Aqueous ammonia (1 ml) was added dropwise to the reaction mixture and the mixture was stirred at room temperature for one hour. The reaction mixture was poured into ice-cold water and extracted with ethyl acetate. The organic layer was washed with a saturated aqueous NaCl solution and dried using anhydrous magnesium sulfate. After filtration, the solvent was evaporated under reduced pressure to obtain the title compound (0.60 g, quantitative) as a colorless powder.

Workup

  1. temperatureunder ice-cooling
  2. stirringby stirring of the mixture at room temperature for 30 minutes
  3. stirringthe mixture was stirred at room temperature for one hour
  4. additionThe reaction mixture was poured into ice-cold water
  5. extractionextracted with ethyl acetate
  6. washThe organic layer was washed with a saturated aqueous NaCl solution
  7. customdried
  8. filtrationAfter filtration
  9. customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-736f8bb1880540ebac0e045ea27e2098
Source dataset
uspto-grants-1999_12
Patent number
US06005116

Reaction notes

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