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

HRID 1870929Notes

Reaction equation

HRID 1870929 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 chloroform-ethyl 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 chloroform-ethyl acetate

Sources & evidence

ORD record
ord-f7e4e0b62973492a833e958848979d6e
Source dataset
uspto-grants-2000_08
Patent number
US06100252

Reaction notes

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