Hydrochloric Acid → HCID 24842607, compound

HRID 2226750Notes

Reaction equation

HRID 2226750 reaction equation
C([O:3][C:4]([C@@H:6]1[CH2:11][CH2:10][CH2:9][N:8]([CH2:12][CH2:13][O:14][N:15]=[C:16]2[C:22]3[CH:23]=[CH:24][CH:25]=[CH:26][C:21]=3[CH2:20][CH2:19][C:18]3[CH:27]=[CH:28][CH:29]=[CH:30][C:17]2=3)[CH2:7]1)=[O:5])C.[OH-].[Na+].[Cl:33]CCl.Cl>C(O)C>[ClH:33].[CH:27]1[C:18]2[CH2:19][CH2:20][C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=3[C:16](=[N:15][O:14][CH2:13][CH2:12][N:8]3[CH2:9][CH2:10][CH2:11][C@@H:6]([C:4]([OH:5])=[O:3])[CH2:7]3)[C:17]=2[CH:30]=[CH:29][CH:28]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 6344DichloromethaneHCID 14798Sodium HydroxideHCID 11069527HCID 11069527, compound

Product 1

HCID 24842607HCID 24842607, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

The above ester (1.0 g, 3.0 mmol) was dissolved in ethanol (25 ml) and a 4 N sodium hydroxide solution (3.4 ml) was added. The mixture was stirred vigorously at room temperature for 22 h. The solvent was evaporated in vacuo to give an oily residue. Dichloromethane (75 ml) was added and the mixture was cooled on an ice-bath. A concentrated hydrochloric acid solution (1.6 ml) was added. The mixture was stirred vigorously for a few minutes and the phases were separated. The organic phase was dried over sodium sulphate and the solvent was evaporated in vacuo. The residue was re-evaporated three times with dichloromethane and once with acetone to give 0.95 g of the title compound as a foam.

Workup

  1. customThe solvent was evaporated in vacuo
  2. customto give an oily residue
  3. temperaturethe mixture was cooled on an ice-bath
  4. stirringThe mixture was stirred vigorously for a few minutes
  5. customthe phases were separated
  6. dry with materialThe organic phase was dried over sodium sulphate
  7. customthe solvent was evaporated in vacuo
  8. customThe residue was re-evaporated three times with dichloromethane

Sources & evidence

ORD record
ord-cfe58e140bc148e5aaba2b5f742543e1
Source dataset
uspto-grants-1994_09
Patent number
US05348965

Reaction notes

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