Urea → HCID 117700823, compound

HRID 1055354Notes

Reaction equation

[CH:1]([CH:3]=[O:4])=[O:2].[NH2:5][C:6]([NH2:8])=[O:7]>>[OH:2][C@@H:1]1[C@H:3]([OH:4])[N:5]2[C:6](=[O:7])[N:8]1[C@H:3]([OH:4])[CH:1]2[OH:2]

Participants

Reactant 2

HCID 1176Urea2×

HCID 7860Glyoxal

Product 1

HCID 117700823HCID 117700823, compound

Conditions

Temperature: 90 °C

Procedure

To 290 g of a 40% solution of glyoxal (116 g active) in a three neck round bottom flask equipped with stirrer, condenser and temperature control added 60 g urea (1 mole) at ambient temperature. After all urea dissolved, the temperature was increased to 90° C. and kept for 60 min until all reactants were consumed and (2R,3S,6R)-2,3,5,6-tetrahydroxy-1,4-diazabicyclo[2.2.1]heptan-7-one product was formed as determined by HPLC. This solution was added to a 50% solution of six moles of dextrose (1080 g) in water at 60° C. After the two solutions mixed, enough water was added to bring the final concentration to 50%.

Workup

customwere consumed

Sources & evidence

ORD record: ord-54bcaadcf75e47439f94297fb554caf6
Source dataset: uspto-grants-2016_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09394431B2

Reaction notes

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