Formic Acid → N-[(3S)-Tetrahydro-2,5-dioxo-3-furanyl]formamide

HRID 1464453Notes

Reaction equation

HRID 1464453 reaction equation
[CH:1](O)=[O:2].C(OC(=O)C)(=O)C.[NH2:11][C@H:12]([C:17]([OH:19])=[O:18])[CH2:13][C:14]([OH:16])=O.O.O.O.O.C([O-])(=O)C.[Mg+2].C([O-])(=O)C>C1(C)C=CC=CC=1.C(O)(=O)C>[CH:1]([NH:11][C@@H:12]1[C:17](=[O:18])[O:19][C:14](=[O:16])[CH2:13]1)=[O:2]

Participants

7

Reactant 4

HCID 284Formic AcidHCID 5960L-Aspartic AcidHCID 7918Acetic AnhydrideHCID 134717Magnesium Acetate Tetrahydrate

Product 1

HCID 11298025N-[(3S)-Tetrahydro-2,5-dioxo-3-furanyl]formamide

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 1140TolueneSolvent2×

Procedure

To 671 ml of formic acid, 226 ml of acetic acid and 226 ml of toluene was added 1437 ml of acetic anhydride. After 910 g of L-aspartic acid and 12.8 g of magnesium acetate tetrahydrate were added to the thus prepared solution, the mixture was kept at a temperature of 45° C. and reacted for 3.5 hours with stirring. To the resulting slurry was added 3970 ml of toluene. After ice-cooling for an hour with stirring, the mixture was filtered, while performing suction, to give 917 g of crystalline N-formyl-L-aspartic anhydride.

Workup

  1. customwas kept at a temperature of 45° C.
  2. customreacted for 3.5 hours
  3. temperatureAfter ice-cooling for an hour
  4. stirringwith stirring
  5. filtrationthe mixture was filtered

Sources & evidence

ORD record
ord-7690de0a59954540a8085e38a4d31c20
Source dataset
uspto-grants-1994_04
Patent number
US05304671

Reaction notes

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