Ethyl Acetate → HCID 178418592, compound

HRID 1080829Notes

Reaction equation

HRID 1080829 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][CH:17]=3)=[C:12](C(=N)NOC(OCC)=O)[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].[N:39]12CCC[N:46]=[C:45]1CCCCC2.[C:50]([O:53]CC)(=[O:52])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:17]=[CH:18][CH:19]=[CH:20][C:21]=3[C:45]3[NH:46][O:53][C:50](=[O:52])[N:39]=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 3

HCID 8857Ethyl AcetateHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 178473669HCID 178473669, compound

Product 1

HCID 178418592HCID 178418592, compoundYield 45%

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-24f776c9503c47da921b1982e5fd4da7
Source dataset
uspto-grants-1996_12
Patent number
US05583141

Reaction notes

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