Acetic Acid → HCID 57090268, compound
Reaction equation
[O:1]([C:8]([NH:10][C@H:11]([C:19]([OH:21])=[O:20])[CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)=[O:9])C1C=CC=CC=1.[C:22]([OH:25])(=[O:24])C>C(#N)C>[C:22]([NH:10][C@H:11]([C:19]([O:21][C:19](=[O:20])[C@H:11]([CH2:12][C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1)[NH:10][C:8]([OH:1])=[O:9])=[O:20])[CH2:12][C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1)([OH:25])=[O:24]Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 80 °C
Procedure
Under a nitrogen atmosphere, 571 mg (2 mmol) of N-phenoxycarbonyl-L-phenylalanine, 360 mg (6 mmol) of acetic acid, and 20 mL of acetonitrile were loaded into a two-necked round bottom flask having a volume of 100 mL and mounted with a Dimroth condenser, and then the mixture was stirred at 80° C. for 29 hours. The fact that N-carboxy-phenylalanine anhydride was obtained in a yield of 99% or more was confirmed by subjecting the reaction mixture to NMR determination. After the reaction mixture had been cooled to room temperature, 2 mL of a 1M aqueous solution of hydrochloric acid and 2,400 mg of activated carbon were added to the resultant, and then the mixture was stirred for 1 hour. The activated carbon was removed by filtration, and then the resultant filtrate was concentrated under reduced pressure. Thus, N-carboxy-phenylalanine anhydride was obtained. An isolation amount and an isolation yield were 302.5 mg and 78%, respectively.
Sources & evidence
- ORD record
- ord-35ba754cd1d8483a8be1760b9d75fb51
- Source dataset
- uspto-grants-2014_06
- Patent number
- US08748650B2
Reaction notes
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