Formic Acid → N-[(3S)-Tetrahydro-2,5-dioxo-3-furanyl]formamide
Reaction equation
[O-2].[Mg+2].[CH:3](O)=[O:4].C(OC(=O)C)(=O)C.[NH2:13][C@H:14]([C:19]([OH:21])=[O:20])[CH2:15][C:16]([OH:18])=O>>[CH:3]([NH:13][C@@H:14]1[C:19](=[O:20])[O:21][C:16](=[O:18])[CH2:15]1)=[O:4]Participants
Procedure
Magnesium oxide (0.121 grams; 0.003 mole) was dissolved in 19.3 grams (0.4 mole) of 95% formic acid under nitrogen. Acetic anhydride (69.3 grams; 0.655 mole) was then added to the solution which was stirred for 10-15 minutes. The temperature of the mixture rose to 40° C. L-aspartic acid (39.93 grams; 0.30 mole) was added to the mixture and the resulting slurry was stirred at about 50° C. for about 6 hours. N-formyl-L-aspartic anhydride was formed at this point as shown by high performance liquid chromatography (HPLC). The mixture was then filtered and washed with 30 grams of acetic acid in order to isolate the N-formyl-L-aspartic anhydride. The yield of the N-formyl-L-aspartic anhydride from the L-aspartic acid was 80%. The N-formyl-L-aspartic anhydride will include some acetic acid, which remains for use as a solvent in the coupling step.
Workup
- customrose to 40° C
- stirringthe resulting slurry was stirred at about 50° C. for about 6 hours
Sources & evidence
- ORD record
- ord-3b5dbfe063f64c5b8c721609f736b720
- Source dataset
- uspto-grants-1990_08
- Patent number
- US04946988
Reaction notes
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