Trifluoroacetic acid → N-Methyl-L-Alanyl-L-Alanine benzyl Ester
Reaction equation
[CH2:1]([O:8][C:9](=[O:26])[C@H:10]([CH3:25])[NH:11][C:12](=[O:24])[C@H:13]([CH3:23])[N:14](C(OC(C)(C)C)=O)[CH3:15])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.FC(F)(F)C(O)=O.C(=O)(O)[O-].[Na+]>ClCCl>[CH2:1]([O:8][C:9](=[O:26])[C@H:10]([CH3:25])[NH:11][C:12](=[O:24])[C@H:13]([CH3:23])[NH:14][CH3:15])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- -10 °C
Procedure
To a stirred solution of 17 g (0.0466 mole) of Boc-N-methyl-L-alanyl-L-alanine benzyl ester in 150 ml of dry dichloromethane, cooled at -10° C., was added 100 ml trifluoroacetic acid, which was previously cooled at -10° C. The reaction mixture was stirred for 16 hours at -5° C., then poured carefully with good stirring into a mixture of 177 g of sodium bicarbonate, ice, and 150 ml of dichloromethane. The organic layer was separated and the aqueous layer was further extracted with another 60 ml of dichloromethane. The combined organic layers were washed with 3×50 ml of saturated sodium bicarbonate solution, dried over manesium sulfate, and evaporated to give 11.6 g (91% of theory) of crude product which was used in step 3 without further purification.
Workup
- additionpoured carefully
- customThe organic layer was separated
- extractionthe aqueous layer was further extracted with another 60 ml of dichloromethane
- washThe combined organic layers were washed with 3×50 ml of saturated sodium bicarbonate solution
- dry with materialdried over manesium sulfate
- customevaporated
- customto give 11.6 g (91% of theory) of crude product which
- customwas used in step 3 without further purification
Sources & evidence
- ORD record
- ord-9d11f8451d2b4cf59e56b9c9ca5c76c8
- Source dataset
- uspto-grants-1990_04
- Patent number
- US04914188
Reaction notes
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