Methanol → methyl (Z)-2-(2-dimethylaminomethylidenaminothiazol-4-yl)-2-pentenoate
Reaction equation
[Cl-].[CH3:2][N:3]([NH+]=CCl)[CH3:4].[O:8]1CCC[CH2:9]1.[NH2:13][C:14]1[S:15][CH:16]=[C:17](/[C:19](=[CH:23]/[CH2:24][CH3:25])/C(O)=O)[N:18]=1.[C:26](=O)([O-])O.[Na+].[CH3:31][OH:32]>>[CH3:2][N:3]([CH:4]=[N:13][C:14]1[S:15][CH:16]=[C:17](/[C:19](=[CH:23]/[CH2:24][CH3:25])/[C:31]([O:8][CH3:9])=[O:32])[N:18]=1)[CH3:26]Participants
Procedure
Dimethylaminochloromethyleneammonium chloride (830 mg, 6.5 mmol) was added to 12 ml of tetrahydrofuran, and the resulting mixture was ice-cooled. Added to the mixture were 196 mg (0.99 mmol) of (Z)-2-(2-aminothiazol-4-yl)-2-pentenoic acid, followed by stirring for 1 hour. Methanol (10 ml) was added thereto. The mixture so obtained was stirred for 30 minutes. The mixture was then poured into 60 ml of a saturated aqueous solution of sodium hydrogencarbonate. The mixture so obtained was extracted three times with 40 ml portions of ethyl acetate. The extract was dried over anhydrous magnesium sulfate and was then filtered. The filtrate was concentrated under reduced pressure. The residue was purified by chromatography on a silica gel column, whereby 177 mg of the title compound were obtained (yield: 67%).
Workup
- temperaturecooled
- additionAdded to the mixture
- customThe mixture so obtained
- stirringwas stirred for 30 minutes
- customThe mixture so obtained
- extractionwas extracted three times with 40 ml portions of ethyl acetate
- dry with materialThe extract was dried over anhydrous magnesium sulfate
- filtrationwas then filtered
- concentrationThe filtrate was concentrated under reduced pressure
- customThe residue was purified by chromatography on a silica gel column
Sources & evidence
- ORD record
- ord-a436bbb478b5451ca5ee158275c2a8b3
- Source dataset
- uspto-grants-1997_07
- Patent number
- US05650518
Reaction notes
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