Hydrogen Bromide → [(2S,5R)-5-(2,4-Dioxo-3,4-dihydropyrimidin-1(2H)-yl)oxolan-2-yl]methyl benzoate

HRID 1031431Notes

Reaction equation

HRID 1031431 reaction equation
[C@@H]1(N2C=CC(=O)NC2=O)O[C@H](CO)[C@@H](O)[C@H]1O.CS(Cl)(=O)=O.CS(O[C@@H]1[C@H](OS(C)(=O)=O)[C@@H](COS(C)(=O)=O)O[C@H]1N1C=CC(=O)NC1=O)(=O)=O.C([O-])(=O)C1C=CC=CC=1.[Na+].Br.C(Br)(=O)C.[C:67]([O:75][CH2:76][C@H:77]1[O:81][C@@H:80]([N:82]2[CH:89]=[CH:88][C:86](=[O:87])[NH:85][C:83]2=[O:84])[C@H:79](Br)[C@@H:78]1OS(C)(=O)=O)(=[O:74])[C:68]1[CH:73]=[CH:72][CH:71]=[CH:70][CH:69]=1>N1C=CC=CC=1.C(N)(=O)C.CN(C)C=O.[Ni].C(O)C.[C].[Pd]>[C:67]([O:75][CH2:76][C@H:77]1[O:81][C@@H:80]([N:82]2[CH:89]=[CH:88][C:86](=[O:87])[NH:85][C:83]2=[O:84])[CH2:79][CH2:78]1)(=[O:74])[C:68]1[CH:73]=[CH:72][CH:71]=[CH:70][CH:69]=1

Participants

14

Reactant 7

HCID 260Hydrogen BromideHCID 6029UridineHCID 10482Acetyl bromideHCID 31297Methanesulfonyl chlorideHCID 517055Sodium BenzoateHCID 14133010HCID 14133010, compoundHCID 18640902HCID 18640902, compound

Product 1

HCID 14308783[(2S,5R)-5-(2,4-Dioxo-3,4-dihydropyrimidin-1(2H)-yl)oxolan-2-yl]methyl benzoateYield 60%

Reagents, catalysts & solvents 6

HCID 935NickelCatalystHCID 178418390HCID 178418390, compoundCatalystHCID 178AcetamideSolventHCID 702EthanolSolventHCID 1049PyridineSolventHCID 6228DimethylformamideSolvent

Procedure

Moreover, 2',3'-dideoxy-uridine or the derivatives thereof being the raw materials can be obtained easily from uridine being a constituting ingredient of ribonucleic acid by known method. For example, in the method described in Chem. Pharm. Bull., 18(3), 554-560, 1970, uridine is treated with methanesulfonyl chloride in pyridine solvent to convert to 2',3',5'-tri-O-methanesulfonyluridine and, by allowing this to react with sodium benzoate in acetamide or dimethylformamide solvent, 2,2'-anhydro-1-(5'-O-benzoyl-3'-O-mesyl-β-arabinosyl)uracil is obtained. This is allowed to react with hydrogen bromide or acetyl bromide to convert to 5'-O-benzoyl-2'-bromo-2'-deoxy-3'-O-mesyluridine and then this is treated with palladium carbon or Raney nickel catalyst in ethanol under atmosphere of hydrogen to obtain 5'-O-benzoyl-2',3'-dideoxy-uridine in a yield of about 60% (Chem. Pharm. Bull., 18(3), 554-560, 1970).

Workup

  1. customis obtained

Sources & evidence

ORD record
ord-7275ae5f3e3848f497c21a180d291825
Source dataset
uspto-grants-1990_09
Patent number
US04954485

Reaction notes

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