Hydrochloric Acid → HCID 22894757, compound
Reaction equation
[CH3:1][CH:2]([C:4]1[N:8]([CH2:9][CH2:10][C@@H:11]([OH:19])[CH2:12][C@@H:13]([OH:18])[CH2:14][C:15]([OH:17])=O)[C:7]([C:20]2[CH:21]=[CH:22][C:23]([F:26])=[CH:24][CH:25]=2)=[C:6]([C:27]2[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=2)[C:5]=1[C:33](NC1C=CC=CC=1)=[O:34])[CH3:3].[OH-:42].[Na+].Cl>C1COCC1.O>[F:26][C:23]1[CH:24]=[CH:25][C:20]([C:7]2[N:8]([CH2:9][CH2:10][C@@H:11]3[CH2:12][C@@H:13]([OH:18])[CH2:14][C:15](=[O:17])[O:19]3)[C:4]([CH:2]([CH3:3])[CH3:1])=[C:5]([C:33]([OH:34])=[O:42])[C:6]=2[C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)=[CH:21][CH:22]=1Participants
6
Reactant 3
Product 1
Reagents, catalysts & solvents 2
Procedure
A solution of atorvastatin (prepared as described in U.S. Pat. Nos. 5,397,792 and 5,446,054) (1 mmol) and NaOH (10 mmol) in THF (30 mL) and water (10 mL) is maintained at 50° C. The progress of the reaction is monitored by tlc. When the reaction is complete, the solution is acidified with dilute HCl and extracted with CH2Cl2. The extract is then dried and evaporated. The residue is dissolved in toluene (50 mL) and the solution is heated at reflux until tlc monitoring shows that formation of the lactone moiety is complete. The solvent is removed under reduced pressure and compound 18 is purified by chromatography.
Workup
- extractionextracted with CH2Cl2
- customThe extract is then dried
- customevaporated
- dissolutionThe residue is dissolved in toluene (50 mL)
- temperaturethe solution is heated
- temperatureat reflux until tlc monitoring
- customThe solvent is removed under reduced pressure and compound 18
- customis purified by chromatography
Sources & evidence
- ORD record
- ord-1e9b095c20a7417592cebecd01ba1992
- Source dataset
- uspto-grants-2002_03
- Patent number
- US06355810B1
Reaction notes
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