Dichloromethane → HCID 70299899, compound

HRID 1378410Notes

Reaction equation

HRID 1378410 reaction equation
Cl.C([O:4][C:5]([CH:7]1[CH2:12][CH2:11][CH2:10][N:9]([CH2:13][CH2:14][CH:15]=[C:16]2[C:22]3[CH:23]=[CH:24][CH:25]=[CH:26][C:21]=3[CH:20]=[CH:19][C:18]3[CH:27]=[CH:28][CH:29]=[CH:30][C:17]2=3)[CH2:8]1)=[O:6])C.[OH-].[Na+:32].ClCCl.C(OCC)(=O)C>C(O)C>[Na+:32].[CH:26]1[C:21]2[CH:20]=[CH:19][C:18]3[CH:27]=[CH:28][CH:29]=[CH:30][C:17]=3[C:16](=[CH:15][CH2:14][CH2:13][N:9]3[CH2:10][CH2:11][CH2:12][CH:7]([C:5]([O-:6])=[O:4])[CH2:8]3)[C:22]=2[CH:23]=[CH:24][CH:25]=1

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 8857Ethyl AcetateHCID 14798Sodium HydroxideHCID 70299924HCID 70299924, compound

Product 1

HCID 70299899HCID 70299899, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

The above ester (4.5 g, 11 mmol) was dissolved in ethanol (80 ml), 32% sodium hydroxide (180 ml) was added and the mixture was heated at reflux for 1 h. To the cooled reaction mixture a mixture of dichloromethane and ethyl acetate was added. The phases were separated and the aqueous phase was treated with activated charcoal and filtered through millipore (0.22 μm). The solvent was evaporated from the filtrate in vacuo and the residue was dissolved in a mixture of water and dichloromethane (1:3). The phases were separated, the organic phase dried (MgSO4) and the solvent evaporated in vacuo. The residue was dissolved in water and freeze-dried to give 3.0 g of the title compound as an amorphous solid.

Workup

  1. temperaturethe mixture was heated
  2. temperatureat reflux for 1 h
  3. customTo the cooled reaction mixture
  4. additionwas added
  5. customThe phases were separated
  6. additionthe aqueous phase was treated with activated charcoal
  7. filtrationfiltered through millipore (0.22 μm)
  8. customThe solvent was evaporated from the filtrate in vacuo
  9. dissolutionthe residue was dissolved in a mixture of water and dichloromethane (1:3)
  10. customThe phases were separated
  11. dry with materialthe organic phase dried (MgSO4)
  12. customthe solvent evaporated in vacuo
  13. dissolutionThe residue was dissolved in water
  14. customfreeze-dried

Sources & evidence

ORD record
ord-1ffa667a2dc54543b11bddaa9c05ce3f
Source dataset
uspto-grants-1997_09
Patent number
US05668129

Reaction notes

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