N-(Benzyloxycarbonyl)aspartic acid → (S)-Benzyl (tetrahydro-2,5-dioxo-3-furyl)carbamate
Reaction equation
[C:1]([NH:11][C@H:12]([C:17]([OH:19])=[O:18])[CH2:13][C:14]([OH:16])=O)([O:3][CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=[O:2]>C(OC(=O)C)(=O)C>[CH2:4]([O:3][C:1]([NH:11][C@@H:12]1[C:17](=[O:18])[O:19][C:14](=[O:16])[CH2:13]1)=[O:2])[C:5]1[CH:6]=[CH:7][CH:8]=[CH:9][CH:10]=1Participants
3
Reactant 1
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 75 °C
Procedure
The above illustrated starting compound which is commercially available N-CBZ aspartic acid (205.7 g, 0.77 mol) was added to acetic anhydride (300 ml). This mixture was stirred at 75° C. for 4 hours. The excess acetic anhydride and acetic acid byproduct were distilled from the mixture under reduced pressure and the residue was recrystallised from hot dichloromethane. The product was collected by filtration, washed with hexane and dried at ambient temperature under reduced pressure to give a white fluffy solid.