N-[beta-(2-furyl)acryloyl]glutamic acid → N-[beta-(2-furyl)acryloyl]glutamic acid anhydride
Reaction equation
[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[CH:6]=[CH:7][C:8]([NH:10][C@H:11]([C:17]([OH:19])=[O:18])[CH2:12][CH2:13][C:14]([OH:16])=O)=[O:9]>C(OC(=O)C)(=O)C>[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[CH:6]=[CH:7][C:8]([NH:10][C@@H:11]1[C:17](=[O:18])[O:19][C:14](=[O:16])[CH2:13][CH2:12]1)=[O:9]Participants
Reactant 1
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 100 °C
Procedure
In 20 ml of acetic anhydride was dissolved 5 g of DL-N-[β-(2-furyl)acryloyl]glutamic acid, and the resulting solution was heated at 100° C. for 15 minutes, after which the excessive acetic anhydride was removed by distillation under reduced pressure to obtain DL-N-[β-(2-furyl)acryloyl]glutamic acid anhydride. This product was added to a mixed solution of 5 ml of di(n-propyl)-amine and 5 ml of water with ice-cooling, and the resulting mixture was subjected to reaction for 2 hours. After completion of the reaction, the reaction mixture was adjusted to pH 4 with diluted hydrochloric acid and extracted with two 20-ml portions of ethyl acetate, and the organic layers were combined and then dried over anhydrous magnesium sulfate. Subsequently, the solvent was removed by distillation under reduced pressure to obtain 4 g (yield 62%) of DL-N2 -[β-(2-furyl)acryloyl]-N1,N1 -di-n-propyl-α-glutamylamide having a melting point of 130°-131° C.
Workup
- customafter which the excessive acetic anhydride was removed by distillation under reduced pressure
Sources & evidence
- ORD record
- ord-855b65090507492b97a746d2c85a6a56
- Source dataset
- uspto-grants-1986_09
- Patent number
- US04610983
Reaction notes
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