Hydrochloric Acid → Diphenylmethyl 7beta-amino-3-[(4-pyridyl)methylthio]-3-cephem-4-carboxylate
Reaction equation
C([NH:3][C@@H:4]1[C:35](=[O:36])[N:6]2[C:7]([C:19]([O:21][CH:22]([C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=3)[C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)=[O:20])=[C:8]([S:11][CH2:12][C:13]3[CH:18]=[CH:17][N:16]=[CH:15][CH:14]=3)[CH2:9][S:10][C@H:5]12)=O.Cl.C(OCC)(=O)C.[OH-].[Na+]>CO>[NH2:3][C@@H:4]1[C:35](=[O:36])[N:6]2[C:7]([C:19]([O:21][CH:22]([C:23]3[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=3)[C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=3)=[O:20])=[C:8]([S:11][CH2:12][C:13]3[CH:14]=[CH:15][N:16]=[CH:17][CH:18]=3)[CH2:9][S:10][C@H:5]12Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Procedure
To a solution of diphenylmethyl 7β-formamido-3-[(4-pyridyl)methylthio]-3-cephem-4-carboxylate (13.70 g, 26.5 m mol) in methanol (65 ml) was added dropwise conc. HCl (11.0 ml) at room temperature and the mixture was stirred at the same temperature for 2.8 hours. The mixture was poured into a mixture of ethyl acetate and ice water and adjusted to pH 7 by addition of 5N NaOH aq. The separated organic layer was washed with water and brine, dried over magnesium sulfate and evaporated in vacuo. The residue was triturated with ethyl acetate to give diphenylmethyl 7β-amino-3-[(4-pyridyl)methylthio]-3-cephem-4-carboxylate (5.16 g).
Workup
- washwas washed with water and brine
- dry with materialdried over magnesium sulfate
- customevaporated in vacuo
- customThe residue was triturated with ethyl acetate
Sources & evidence
- ORD record
- ord-19382d95f85649178a32e4f082b30479
- Source dataset
- uspto-grants-2002_10
- Patent number
- US06468995B1
Reaction notes
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