1,8-Diazabicyclo(5.4.0)undec-7-ene → HCID 54542309, compound

HRID 1603537Notes

Reaction equation

HRID 1603537 reaction equation
[CH2:1]([O:5][C:6](=[O:29])[C:7]1[CH:12]=[C:11]([CH2:13][CH2:14][C:15]2[CH:20]=[C:19]([O:21][CH3:22])[CH:18]=[CH:17][C:16]=2[O:23][CH3:24])[CH:10]=[CH:9][C:8]=1[NH:25][C:26](=[O:28])[CH3:27])[CH2:2]CC.[Br-].[Li+].N12CCCN=C1CCCCC2>C(O)C>[CH2:1]([O:5][C:6](=[O:29])[C:7]1[CH:12]=[C:11]([CH2:13][CH2:14][C:15]2[CH:20]=[C:19]([O:21][CH3:22])[CH:18]=[CH:17][C:16]=2[O:23][CH3:24])[CH:10]=[CH:9][C:8]=1[NH:25][C:26](=[O:28])[CH3:27])[CH3:2]

Participants

5

Reactant 3

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 82050Lithium BromideHCID 53984238HCID 53984238, compound

Product 1

HCID 54542309HCID 54542309, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 93 mg of 5-[2-(2,5-dimethoxyphenyl)ethyl]-2-acetylamino-benzoic acid butylester, 100 mg of lithium bromide, 55 mg of 1,8-diazabicyclo[5.4.0]undec-7-en and 4 ml of dry ethanol is heated to reflux for 3 hours. After neutralisation with 0.1 N aqueous hydrochloric acid, the mixture is extracted with ethyl acetate. The combined organic extracts are dried over magnesium sulfate and concentrated in vacuo. The pure title compound is obtained by silica gel chromatography (hexane/ethyl acetate=6/1) as colourless crystals. mp: 93°.

Workup

  1. temperatureis heated
  2. temperatureto reflux for 3 hours
  3. extractionAfter neutralisation with 0.1 N aqueous hydrochloric acid, the mixture is extracted with ethyl acetate
  4. dry with materialThe combined organic extracts are dried over magnesium sulfate
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-f153072bb23e4b3a8ff9b3b2d0d18fd5
Source dataset
uspto-grants-1999_11
Patent number
US05990116

Reaction notes

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