Pentafluorophenol → 5-Oxo-pyrrolidine-3-carboxylic acid pentafluorophenyl ester
Reaction equation
[F:1][C:2]1[C:7]([OH:8])=[C:6]([F:9])[C:5]([F:10])=[C:4]([F:11])[C:3]=1[F:12].[O:13]=[C:14]1[NH:18][CH2:17][CH:16]([C:19](O)=[O:20])[CH2:15]1>C(OCC)(=O)C>[F:1][C:2]1[C:7]([O:8][C:19]([CH:16]2[CH2:15][C:14](=[O:13])[NH:18][CH2:17]2)=[O:20])=[C:6]([F:9])[C:5]([F:10])=[C:4]([F:11])[C:3]=1[F:12]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
To a suspension of 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride EDCI (18.5 mg, 0.096 mmol) in 2 mL ethyl acetate was added pentafluorophenol (35.6 mg, 0.193 mmol) at 0° C. After 10 minutes, 5-oxo-pyrrolidine-3-carboxylic acid 16 (33.9 mg, 0.064 mmol) was added at 0° C. and the reaction mixture was stirred for 1 hour at room temperature. After evaporation of the solvent, the crude product was purified by chromatography on silica gel (ethyl acetate:hexane=1:2) to yield the corresponding 5-oxo-pyrrolidine-3-carboxylic acid pentafluorophenyl ester 17 as a colourless oil (40.1 mg, 89.80%).