Methanol → 4-Aminothiazole-5-carboxylic acid ethyl ester
Reaction equation
CO.C1COCC1.[CH2:8]([O:10][C:11]([C:13]1[S:17][C:16](S(C)(=O)=O)=[N:15][C:14]=1[NH2:22])=[O:12])[CH3:9].[BH4-].[Na+]>O.C(OCC)(=O)C>[CH2:8]([O:10][C:11]([C:13]1[S:17][CH:16]=[N:15][C:14]=1[NH2:22])=[O:12])[CH3:9]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Procedure
To 1 liter of a methanol:THF=1:1 mixed solvent solution containing 34.5 g of 4-amino-2-methanesulfonylthiazole-5-carboxylic acid ethyl ester, 10.4 g of sodium borohydride was added in small portions over a period of 20 minutes at room temperature. The reaction mixture was stirred at room temperature for 2 hours, and then was poured into 8 liters of ethyl acetate and 4 liters of water. The organic layer was washed with 3 liters of water and 3 liters of saturated brine, and the aqueous layer was extracted with ethyl acetate again. The organic layers were combined and dried over anhydrous magnesium sulfate. The desiccating agent was removed by filtration, and the filtrate was concentrated under reduced pressure to give the title compound (19.3 g) as a light yellow solid.
Workup
- additionwas added in small portions over a period of 20 minutes at room temperature
- washThe organic layer was washed with 3 liters of water and 3 liters of saturated brine
- extractionthe aqueous layer was extracted with ethyl acetate again
- dry with materialdried over anhydrous magnesium sulfate
- customThe desiccating agent was removed by filtration
- concentrationthe filtrate was concentrated under reduced pressure
Sources & evidence
- ORD record
- ord-ec707d28489c47b1bccd6cd1b7585fc6
- Source dataset
- uspto-grants-2010_10
- Patent number
- US07816522B2
Reaction notes
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