Triethylamine → HCID 19846218, compound

HRID 2351822Notes

Reaction equation

HRID 2351822 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([O:8][C:9]2[CH:10]=[C:11]([CH:18]=[CH:19][CH:20]=2)[CH2:12][CH:13]([C:15]([OH:17])=[O:16])[NH2:14])=[N:6][CH:7]=1.C(N(CC)CC)C.[C:28]([O:32][C:33](ON=C(C1C=CC=CC=1)C#N)=[O:34])([CH3:31])([CH3:30])[CH3:29].C(OCC)(=O)C>O.O1CCOCC1>[C:28]([O:32][C:33]([NH:14][CH:13]([C:15]([OH:17])=[O:16])[CH2:12][C:11]1[CH:18]=[CH:19][CH:20]=[C:9]([O:8][C:5]2[CH:4]=[CH:3][C:2]([Br:1])=[CH:7][N:6]=2)[CH:10]=1)=[O:34])([CH3:31])([CH3:30])[CH3:29]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 938652-(tert-Butoxycarbonyloxyimino)-2-phenylacetonitrileHCID 53725742HCID 53725742, compound

Product 1

HCID 19846218HCID 19846218, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 312751,4-DioxaneSolvent2×

Procedure

The compound (VII) (4.20 g) obtained above was suspended in water (40 ml) and 1,4-dioxane (10 ml) and triethylamine (6.0 ml) was further added. To this solution, a solution of 2-t-butoxycarbonyloxyimino-2-phenylacetnitrile (VIII) (3.06 g) in 1,4-dioxane (20 ml) was added at once at room temperature. The mixture was allowed to react at room temperature for 3 hours. Water (40 ml) and ethyl acetate (30 ml) were added to remove the unreacted compound (VIII). The aqueous layer was made weak acidic with citric acid. The separated oily product was extracted with ethyl acetate, followed by washing with water and drying. After distilling off the solvent in vacuo, the desired compound (I) (5.04 g), which was confirmed by NMR and IR analyses, was obtained in the amorphous state.

Workup

  1. customto react at room temperature for 3 hours
  2. customto remove the unreacted compound (VIII)
  3. extractionThe separated oily product was extracted with ethyl acetate
  4. washby washing with water
  5. customdrying
  6. distillationAfter distilling off the solvent in vacuo
  7. customwas obtained in the amorphous state

Sources & evidence

ORD record
ord-90647e4998b744edab5ba87317b522e6
Source dataset
uspto-grants-1989_10
Patent number
US04873253

Reaction notes

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