Ethyl diazoacetate → HCID 69988095, compound

HRID 1357808Notes

Reaction equation

HRID 1357808 reaction equation
[CH2:1]([N:8]([CH3:29])[C:9]1[CH:14]=[CH:13][C:12]([C:15]([CH3:25])([CH2:23][OH:24])[C:16]([N:18]2[CH2:22][CH2:21][CH2:20][CH2:19]2)=[O:17])=[CH:11][C:10]=1[N+:26]([O-:28])=[O:27])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[N+](=[CH:32][C:33]([O:35][CH2:36][CH3:37])=[O:34])=[N-]>C(Cl)Cl>[CH2:1]([N:8]([CH3:29])[C:9]1[CH:14]=[CH:13][C:12]([C:15]([CH3:25])([CH2:23][O:24][CH2:32][C:33]([O:35][CH2:36][CH3:37])=[O:34])[C:16]([N:18]2[CH2:19][CH2:20][CH2:21][CH2:22]2)=[O:17])=[CH:11][C:10]=1[N+:26]([O-:28])=[O:27])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 12192Ethyl diazoacetateHCID 18188148HCID 18188148, compound

Product 1

HCID 69988095HCID 69988095, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 8.0 g (20 mmol) of 2-[4-(N-benzyl-methylamino)-3-nitro-phenyl]-2-methyl-3-hydroxy-1-pyrrolidino-propan-1-one and 5 ml (48 mmol) of ethyl diazoacetate in 50 ml of methylene chloride is mixed with 2.0 ml of boron trifluoride-diethylether complex (16 mmol) at room temperature and refluxed for 14 hours. After cooling, the reaction solution is stirred into ice water and the organic phase is separated off. The aqueous phase is extracted three times with methylene chloride, the combined organic phases are washed with saline solution, dried over sodium sulphate and concentrated by evaporation. The residue is dissolved in ethyl acetate and purified on silica gel, extracting initially with petroleum ether, then with petroleum ether/ethyl acetate (1:1). The uniform fractions are combined and concentrated by evaporation.

Workup

  1. temperaturerefluxed for 14 hours
  2. temperatureAfter cooling
  3. customthe organic phase is separated off
  4. extractionThe aqueous phase is extracted three times with methylene chloride
  5. washthe combined organic phases are washed with saline solution
  6. dry with materialdried over sodium sulphate
  7. concentrationconcentrated by evaporation
  8. dissolutionThe residue is dissolved in ethyl acetate
  9. custompurified on silica gel
  10. extractionextracting initially with petroleum ether
  11. concentrationconcentrated by evaporation

Sources & evidence

ORD record
ord-e22fea20a35d4ab9a85693164914fbb7
Source dataset
uspto-grants-2003_07
Patent number
US06593355B2

Reaction notes

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