Hydrochloric Acid → HCID 24842602, compound
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]2[C:23]3[CH:24]=[C:25]([Cl:28])[CH:26]=[CH:27][C:22]=3[CH2:21][CH2:20][C:19]3[CH:29]=[CH:30][C:31]([Cl:33])=[CH:32][C:18]2=3)[CH2:7]1)=[O:5])C.[OH-].[Na+].Cl>C(O)C>[ClH:28].[Cl:28][C:25]1[CH:26]=[CH:27][C:22]2[CH2:21][CH2:20][C:19]3[CH:29]=[CH:30][C:31]([Cl:33])=[CH:32][C:18]=3[N:17]([CH2:16][CH2:15][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:23]=2[CH:24]=1Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
The above ester (1.5 g, 3.1 mmol) was dissolved in ethanol (20 ml). A 4 N aqueous sodium hydroxide solution (2.3 ml) was added and the mixture was stirred at ambient temperature for 3 h. A concentrated aqueous hydrochloric acid solution (3 ml) was added until pH 1 and the mixture was extracted with dichloromethane (300 ml). The phases were separated and the organic phase was washed with water (10 ml) and dried over magnesium sulphate. The solvent was evaporated in vacuo and the residue re-evaporated with acetone. The foamy residue was dissolved in acetone (20 ml) and left for crystallization. This afforded 1.25 g of the title compound as a solid.
Workup
- extractionthe mixture was extracted with dichloromethane (300 ml)
- customThe phases were separated
- washthe organic phase was washed with water (10 ml)
- dry with materialdried over magnesium sulphate
- customThe solvent was evaporated in vacuo
- customthe residue re-evaporated with acetone
- dissolutionThe foamy residue was dissolved in acetone (20 ml)
- waitleft for crystallization
Sources & evidence
- ORD record
- ord-2e3466ad5b7b4582b87a28cf8d452c7a
- Source dataset
- uspto-grants-1994_09
- Patent number
- US05348965
Reaction notes
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