Formic Acid → N-[(3S)-Tetrahydro-2,5-dioxo-3-furanyl]formamide
Reaction equation
[C:1](OC(=O)C)(=[O:3])C.C(O)=O.[NH2:11][C@H:12]([C:17]([OH:19])=[O:18])[CH2:13][C:14]([OH:16])=O>C1(C)C=CC=CC=1>[CH:1]([NH:11][C@@H:12]1[C:17](=[O:18])[O:19][C:14](=[O:16])[CH2:13]1)=[O:3]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
Into a 500 ml four-necked flask with a stirrer, a dropping funnel, a Dimroth condenser, and a thermometer, 112.5 g (1.10 mol) of acetic anhydride were introduced, and 30 g (0.65 mol) of formic acid were added dropwise thereto while stirring at room temperature. After stirring was performed at room temperature for 2 hours, 66.5 g (0.5 mol) of L-aspartic acid with an optical purity of 99.5% e.e. were added thereto, the temperature was increased to 60 to 70° C., and stirring was performed for 10 hours. The temperature was decreased to room temperature while stirring, and 80 g of toluene were further added thereto, followed by stirring. The precipitated crystal was subjected to filtration under reduced pressure and was rinsed with 10 g of toluene. The crystal was subjected to vacuum drying, and thus 60.1 g of N-formyl-L-aspartic anhydride was obtained. The chemical purity was 99%, and the optical purity was 99% e.e. or more.
Workup
- stirringAfter stirring
- temperaturethe temperature was increased to 60 to 70° C.
- stirringstirring
- waitwas performed for 10 hours
- customwas decreased to room temperature
- stirringwhile stirring
- stirringby stirring
- filtrationThe precipitated crystal was subjected to filtration under reduced pressure
- washwas rinsed with 10 g of toluene
- customdrying
Sources & evidence
- ORD record
- ord-c559b2e54a3c45ec9b50c80ef77b7613
- Source dataset
- uspto-grants-2002_02
- Patent number
- US06348600B1
Reaction notes
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