1,8-Diazabicyclo(5.4.0)undec-7-ene → HCID 178418592, compound

HRID 1707720Notes

Reaction equation

HRID 1707720 reaction equation
[CH2:1]([O:3][C:4]1[N:8]([CH2:9][C:10]2[CH:15]=[CH:14][C:13]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=3[C:22](=[NH:30])[NH:23][O:24][C:25]([O:27]CC)=O)=[CH:12][CH:11]=2)[C:7]2[C:31]([C:35]([O:37][CH3:38])=[O:36])=[CH:32][CH:33]=[CH:34][C:6]=2[N:5]=1)[CH3:2].N12CCCN=C1CCCCC2>C(OCC)(=O)C>[CH2:1]([O:3][C:4]1[N:8]([CH2:9][C:10]2[CH:11]=[CH:12][C:13]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=3[C:22]3[NH:23][O:24][C:25](=[O:27])[N:30]=3)=[CH:14][CH:15]=2)[C:7]2[C:31]([C:35]([O:37][CH3:38])=[O:36])=[CH:32][CH:33]=[CH:34][C:6]=2[N:5]=1)[CH3:2]

Participants

4

Reactant 2

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 178418570HCID 178418570, compound

Product 1

HCID 178418592HCID 178418592, compoundYield 57.6%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
80 °C

Procedure

The crude crystals (4.0 g) obtained in Example (57b) was dissolved in ethyl acetate (50 ml). To the solution was added 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU, 3.2 g), and the mixture was stirred for 2 hours at 80° C. The reaction mixture was partitioned between ethyl acetate (50 ml) and 1N HCl (20 ml). The organic layer was washed with water, dried and concentrated to dryness. The residue was crystallized from chloroformethyl acetate to afford the title compound as colorless prisms (2.1 g, 45%), which was in agreement with that obtained in Example (1d).

Workup

  1. customThe reaction mixture was partitioned between ethyl acetate (50 ml) and 1N HCl (20 ml)
  2. washThe organic layer was washed with water
  3. customdried
  4. concentrationconcentrated to dryness
  5. customThe residue was crystallized from chloroformethyl acetate

Sources & evidence

ORD record
ord-0f78cd3cfd034fa3ad046814c301f51f
Source dataset
uspto-grants-1994_10
Patent number
US05354766

Reaction notes

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