Sodium Hydroxide → HCID 67768566, 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[CH2:23][C:22]3[CH:24]=[CH:25][CH:26]=[CH:27][C:21]=3[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+]>C(O)C>[CH:4]([OH:5])=[O:3].[CH:28]1[C:19]2[CH2:20][C:21]3[CH:27]=[CH:26][CH:25]=[CH:24][C:22]=3[CH2:23][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:18]=2[CH:31]=[CH:30][CH:29]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 50 °C
Procedure
The above ester (1.0 g, 2.4 mmol) was dissolved in ethanol (25 ml) and a 2 N aqueous sodium hydroxide solution (4.7 ml) was added. The mixture was heated at 50° C. with stirring for 2.5 h. The volatiles were evaporated in vacuo and dichloromethane (100 ml) was added to the residue. The mixture was cooled on an ice-bath and a concentrated aqueous hydrochloric acid solution (1.2 ml) was added dropwise with vigorous stirring. The phases were separated and the organic phase was dried over magnesium sulphate. The solvent was evaporated in vacuo and the residue re-evaporated several times with acetone.
Workup
- customThe volatiles were evaporated in vacuo and dichloromethane (100 ml)
- additionwas added to the residue
- temperatureThe mixture was cooled on an ice-bath
- additiona concentrated aqueous hydrochloric acid solution (1.2 ml) was added dropwise with vigorous stirring
- customThe phases were separated
- dry with materialthe organic phase was dried over magnesium sulphate
- customThe solvent was evaporated in vacuo
- customthe residue re-evaporated several times with acetone
Sources & evidence
- ORD record
- ord-e5694b0197d64b9198c6533d74c3ab5e
- Source dataset
- uspto-grants-1994_09
- Patent number
- US05348965
Reaction notes
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