Hydrochloric Acid → 2-[(tert-Butoxycarbonyl)amino]-4-(trifluoromethyl)-1,3-thiazole-5-carboxylic acid
Reaction equation
C([O:3][C:4]([C:6]1[S:10][C:9]([NH:11][C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])=[N:8][C:7]=1[C:19]([F:22])([F:21])[F:20])=[O:5])C.[OH-].[K+].O.Cl>C1COCC1.C(O)C>[C:15]([O:14][C:12]([NH:11][C:9]1[S:10][C:6]([C:4]([OH:5])=[O:3])=[C:7]([C:19]([F:21])([F:22])[F:20])[N:8]=1)=[O:13])([CH3:18])([CH3:16])[CH3:17]Participants
7
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 60 °C
Procedure
To a solution of 2-tert-Butoxycarbonylamino-4-trifluoromethyl-thiazole-5-carboxylic acid ethyl ester (6.67 g, 19.60 mmol) in THF (42 mL) and ethanol (63 mL) was added aqueous 6N potassium hydroxide (100 mL) cautiously at 25° C. and heated at 60° C. for 20 h. The reaction mixture was cooled to room temperature, added water (200 mL), cooled in an ice bath with stirring at 0° C., cautiously acidified to pH 1 with concentrated HCl and extracted with ethyl acetate (3×200 mL). The organic layers were combined, washed with brine (200 mL), dried over MgSO4, filtered and concentrated under reduced pressure to give 2-tert-Butoxycarbonylamino-4-trifluoromethyl-thiazole-5-carboxylic acid (6.03 g, 100%) as a pale yellow solid.
Workup
- temperatureThe reaction mixture was cooled to room temperature
- temperaturecooled in an ice bath
- extractionextracted with ethyl acetate (3×200 mL)
- washwashed with brine (200 mL)
- dry with materialdried over MgSO4
- filtrationfiltered
- concentrationconcentrated under reduced pressure
Sources & evidence
- ORD record
- ord-047687dd14944cc89896bed77d98723f
- Source dataset
- uspto-grants-2013_03
- Patent number
- US08404859B2
Reaction notes
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