Phosphorus oxychloride → HCID 19596725, compound

HRID 612875Notes

Reaction equation

HRID 612875 reaction equation
[C:1]([O:5][C:6]([NH:8][CH2:9][CH2:10][O:11][C:12]1[C:16]([C:17](=O)[NH2:18])=[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].P(Cl)(Cl)(Cl)=O>CN(C)C=O>[C:1]([O:5][C:6]([NH:8][CH2:9][CH2:10][O:11][C:12]1[C:16]([C:17]#[N: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])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 19596580HCID 19596580, compound

Product 1

HCID 19596725HCID 19596725, compoundYield 78%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

3-(2-(N-tert-Butoxycarbonylamino)ethoxy)-4-carbamoyl-5-phenylisoxazole (0.38 g) was dissolved in dimethylformamide (4 ml), and phosphorus oxychloride (0.11 ml) was added dropwise thereto at 5° C. under a nitrogen atmosphere, followed by stirring of the mixture at room temperature for 30 minutes. 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 over anhydrous magnesium sulfate. After filtration, the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (eluent: hexane/ethyl acetate=3/1) to obtain the title compound (0.28 g, 78%) as a colorless solid.

Workup

  1. customat 5° C.
  2. additionThe reaction mixture was poured into ice-cold water
  3. extractionextracted with ethyl acetate
  4. washThe organic layer was washed with a saturated aqueous NaCl solution
  5. dry with materialdried over anhydrous magnesium sulfate
  6. filtrationAfter filtration
  7. customthe solvent was evaporated under reduced pressure
  8. customThe residue was purified by silica gel column chromatography (eluent: hexane/ethyl acetate=3/1)

Sources & evidence

ORD record
ord-175a78c789494ef49f00cf250ce98e54
Source dataset
uspto-grants-1999_12
Patent number
US06005116

Reaction notes

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