Hydrochloric Acid → HCID 67713872, compound

HRID 1451510Notes

Reaction equation

HRID 1451510 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][CH2:15][CH2:16][N:17]([C:22]2[CH:27]=[CH:26][C:25]([F:28])=[CH:24][C:23]=2[Cl:29])[CH2:18][CH:19]([CH3:21])[CH3:20])[CH2:7]1)=[O:5])C.[OH-].[Na+].Cl>C(O)C>[ClH:29].[Cl:29][C:23]1[CH:24]=[C:25]([F:28])[CH:26]=[CH:27][C:22]=1[N:17]([CH2:16][CH2:15][O:14][CH2:13][CH2:12][N:8]1[CH2:9][CH2:10][CH2:11][C@@H:6]([C:4]([OH:5])=[O:3])[CH2:7]1)[CH2:18][CH:19]([CH3:21])[CH3:20]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 53801152HCID 53801152, compound

Product 1

HCID 67713872HCID 67713872, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

The above ester (13.1 g, 31 mmol) was dissolved in ethanol (50 ml), 2N sodium hydroxide (50 ml) was added and the mixture was heated at reflux for 1 h. After cooling to ambient temperature pH was adjusted to 0 with concentrated hydrochloric acid. The resulting mixture was washed with dichloromethane (2×100 ml) and pH in the aqueous phase was adjusted to 2.5 with 1N sodium hydroxide. The mixture was extracted with dichloromethane (100 ml) and the solvent was evaporated from the organic phase in vacuo. To the residue was added acetone (50 ml) and diethylether (50 ml) and the mixture was left for crystallisation. This afforded 5.8 g of the title compound.

Workup

  1. temperaturethe mixture was heated
  2. temperatureat reflux for 1 h
  3. washThe resulting mixture was washed with dichloromethane (2×100 ml)
  4. extractionThe mixture was extracted with dichloromethane (100 ml)
  5. customthe solvent was evaporated from the organic phase in vacuo
  6. additionTo the residue was added acetone (50 ml) and diethylether (50 ml)
  7. waitthe mixture was left for crystallisation

Sources & evidence

ORD record
ord-ca8900e805614d67a3c989341b2c0c45
Source dataset
uspto-grants-1997_02
Patent number
US05604242

Reaction notes

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