Trifluoroacetic acid → 1-(2-Amino-1,3-thiazol-4-yl)propan-1-one
Reaction equation
C(OC(=O)[NH:7][C:8]1[S:9][CH:10]=[C:11]([C:13](=[O:16])[CH2:14][CH3:15])[N:12]=1)(C)(C)C.FC(F)(F)C(O)=O>ClCCl>[NH2:7][C:8]1[S:9][CH:10]=[C:11]([C:13](=[O:16])[CH2:14][CH3:15])[N:12]=1Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
(4-Propionyl-thiazol-2-yl)-carbamic acid tert-butyl ester (5.0 g, 19.5 mmol) was suspended in dichloromethane (100 mL) at 0° C. Trifluoroacetic acid (100 mL) was added and the mixture was stirred at 0° C. for 1.5 hours. The cooling bath was removed and stirring was continued for 1 hour prior to concentration of the reaction mixture in vacuo. The residue was triturated with ether and filtered. The solid was dissolved in a mixture of dichloromethane and saturated aqueous sodium bicarbonate solution. The organic layer was separated and the aqueous layer was extracted with dichloromethane. The combined organic extracts were washed with brine, dried over sodium sulfate and evaporated to give 1-(2-amino-thiazol-4-yl)-propan-1-one (2.3 g, 75%).
Workup
- customThe cooling bath was removed
- stirringstirring
- waitwas continued for 1 hour
- customThe residue was triturated with ether
- filtrationfiltered
- dissolutionThe solid was dissolved in a mixture of dichloromethane and saturated aqueous sodium bicarbonate solution
- customThe organic layer was separated
- extractionthe aqueous layer was extracted with dichloromethane
- washThe combined organic extracts were washed with brine
- dry with materialdried over sodium sulfate
- customevaporated
Sources & evidence
- ORD record
- ord-131e9f6cf7aa489aaba0f33c4226b354
- Source dataset
- uspto-grants-2008_09
- Patent number
- US07427635B2
Reaction notes
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