Trifluoroacetic acid → (S)-4-(trifluoroacetylamino)-5-fluoropentanoic acid, methyl ester
Reaction equation
[F:1][C:2]([F:7])([F:6])[C:3](O)=[O:4].Cl.[CH3:9][O:10][C:11](=[O:18])[CH2:12][CH2:13][C@H:14]([NH2:17])[CH2:15][F:16].FC(F)(F)C(OC(=O)C(F)(F)F)=O>C(N(CC)CC)C>[F:1][C:2]([F:7])([F:6])[C:3]([NH:17][C@H:14]([CH2:15][F:16])[CH2:13][CH2:12][C:11]([O:10][CH3:9])=[O:18])=[O:4]Participants
5
Conditions
- Temperature
- -10 °C
Procedure
0.28 g of triethylamine and 0.96 ml of trifluoroacetic acid were added to 0.28 g of 4, and the mixture was cooled to -10° C. 0.25 ml of trifluoroacetic anhydride was added drop-by-drop. The resulting mixture was allowed to warm to room temperature and stirred for 90 minutes. Volatile materials were evaporated under reduced pressure, and the residue, an oil, was eluted through a column of florisil, using ethyl acetate as eluent. After evaporation of the solvent, the resulting oil was stripped under reduced pressure to give 8, as a brown solid.
Workup
- temperatureto warm to room temperature
- customVolatile materials were evaporated under reduced pressure
- washthe residue, an oil, was eluted through a column of florisil
- customAfter evaporation of the solvent
- customto give 8
Sources & evidence
- ORD record
- ord-fce0879db7c44d69a1c19be31f533d77
- Source dataset
- uspto-grants-1985_07
- Patent number
- US04528028
Reaction notes
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