Acetic Acid → Uridine

HRID 1598940Notes

Reaction equation

HRID 1598940 reaction equation
[CH:1]1[C:15](=[O:16])[N:14]=[C:13]2[N:3]([C@@H:4]3[O:8][C@H:7]([CH2:9][OH:10])[C@@H:6]([OH:11])[C@@H:5]3[O:12]2)[CH:2]=1.C[O-].[Mg+2].C[O-].C(O)(=[O:24])C>CO>[C@@H:4]1([N:3]2[CH:2]=[CH:1][C:15](=[O:16])[NH:14][C:13]2=[O:12])[O:8][C@H:7]([CH2:9][OH:10])[C@@H:6]([OH:11])[C@H:5]1[OH:24]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 164537Methanol, magnesium salt (2:1)HCID 8061382,2'-Anhydrouridine

Product 1

HCID 6029Uridine

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
150 °C

Procedure

2,2'-anhydro uridine (1, 75 g, 331.56 mmol) was added to the freshly prepared solution of 15% magnesium methoxide (1218.75 ml, 1.66 mol) in methanol. The mixture was refluxed at 150° C. for five hours. The mixture was cooled down to room temperature and then to 5° C. on ice bath. The pH was adjusted to 7 by using glacial acetic acid. The solution was roto-evaporated to a foam. This solid was refluxed with ethyl alcohol (1500 ml) for two hours. The solid was filtered and filtrate was roto-evaporated to a solid mass. The isolated yield of the compound was 78.75 g (92%). The product was >95% pure by HPLC. The yield after quantitation against uridine was 89%. The structure of the compound was confirmed by 1H-NMR and elemental analysis. Table 1 shows the PMR results of the compounds.

Workup

  1. temperatureThe mixture was cooled down to room temperature
  2. customto 5° C.
  3. customThe solution was roto-evaporated to a foam
  4. temperatureThis solid was refluxed with ethyl alcohol (1500 ml) for two hours
  5. filtrationThe solid was filtered
  6. customfiltrate was roto-evaporated to a solid mass

Sources & evidence

ORD record
ord-44f8875537184b93b94f5ff347df52b3
Source dataset
uspto-grants-1998_04
Patent number
US05739314

Reaction notes

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