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

HRID 344823Notes

Reaction equation

HRID 344823 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.C(O)(C)C>>[CH:3]([NH:13][C@@H:14]1[C:19](=[O:20])[O:21][C:16](=[O:18])[CH2:15]1)=[O:4]

Participants

6

Reactant 5

HCID 284Formic AcidHCID 3776IsopropanolHCID 5960L-Aspartic AcidHCID 7918Acetic Anhydride2×HCID 6850729Magnesium monoxide

Product 1

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

Conditions

Temperature
50 °C

Procedure

0.12 grams (0.003 mole) of magnesium oxide, a catalyst, was dissolved in 16 milliliters (ml) (0.405 mole) of 95% formic acid. 60.2 ml of acetic anhydride was then added to the aforementioned solution which was heated to 35°-40° C. for 10-15 minutes. Subsequently, 39.93 grams (0.3 mole) of L-aspartic acid was added and this mixture was stirred for 2.5 hours at 50±2° C. At this point, an additional 8.6 ml of acetic anhydride was added and the reaction continued for an additional 2.5 hours at 50±2° C. 9.2 ml (0.120 mole) of isopropyl alcohol was then added to the reaction mixture and heating was continued for an additional two hours. N-formyl aspartic anhydride was formed at this point as shown by high performance liquid chromatography (HPLC).

Workup

  1. temperaturewas heated to 35°-40° C. for 10-15 minutes
  2. waitthe reaction continued for an additional 2.5 hours at 50±2° C
  3. temperatureheating
  4. waitwas continued for an additional two hours

Sources & evidence

ORD record
ord-bf3f54e412e742cab7a9fda373bc07c9
Source dataset
uspto-grants-1991_10
Patent number
US05053532

Reaction notes

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