Hydrochloric Acid → HCID 140373087, compound

HRID 2226757Notes

Reaction equation

HRID 2226757 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]=[CH:16][CH:17]2[C:23]3[CH:24]=[CH:25][CH:26]=[CH:27][C:22]=3[CH2:21][CH2:20][C:19]3[CH:28]=[CH:29][CH:30]=[CH:31][C:18]2=3)[CH2:7]1)=[O:5])C.[OH-].[Na+].[Cl:34]CCl.Cl>C(O)C>[ClH:34].[CH:28]1[C:19]2[CH2:20][CH2:21][C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=3[CH:17](/[CH: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:18]=2[CH:31]=[CH:30][CH:29]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 6344DichloromethaneHCID 14798Sodium HydroxideHCID 53936468HCID 53936468, compound

Product 1

HCID 140373087HCID 140373087, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

The above ester (5.0 g, 12 mmol) was dissolved in ethanol (100 ml) and a 2 N aqueous sodium hydroxide solution (27 ml) was added. The mixture was stirred at room temperature for 16 h. The solvent was evaporated in vacuo to give an oily residue. Dichloromethane (160 ml) was added and the mixture was cooled on an ice-bath. A concentrated hydrochloric acid solution (5.5 ml) was added. The mixture was stirred vigorously for a few minutes and the phases were separated. The organic phase was dried over magnesium sulphate and the solvent was evaporated in vacuo to give 4.1 g of the title compound as a foam. The material isolated consists of an approx. 1:5 mixture of the E/Z isomers.

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 magnesium sulphate
  7. customthe solvent was evaporated in vacuo

Sources & evidence

ORD record
ord-bbb38ef1b0ee4cc3acc90793a1d0ed7a
Source dataset
uspto-grants-1994_09
Patent number
US05348965

Reaction notes

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