Pentafluorophenol → 5-Oxo-pyrrolidine-3-carboxylic acid pentafluorophenyl ester

HRID 2167181Notes

Reaction equation

HRID 2167181 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

HCID 13041PentafluorophenolHCID 167851365-Oxopyrrolidine-3-carboxylic acid

Product 1

HCID 866401555-Oxo-pyrrolidine-3-carboxylic acid pentafluorophenyl esterYield 212.3%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

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%).

Workup

  1. customAfter evaporation of the solvent
  2. customthe crude product was purified by chromatography on silica gel (ethyl acetate:hexane=1:2)

Sources & evidence

ORD record
ord-93bcd42e2eab4e99ad90645d1c9e5c11
Source dataset
uspto-grants-2015_06
Patent number
US09045414B2

Reaction notes

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