Acetic Anhydride → [(2R,3R,4R,5R)-3,4-diacetyloxy-5-(6-oxo-3H-purin-9-yl)oxolan-2-yl]methyl acetate

HRID 981724Notes

Reaction equation

HRID 981724 reaction equation
[C@@H:1]1([N:10]2[C:19]3[N:18]=[CH:17][N:16]=[C:14]([OH:15])[C:13]=3[N:12]=[CH:11]2)[O:9][C@H:6]([CH2:7][OH:8])[C@@H:4]([OH:5])[C@H:2]1[OH:3].C(O[C:24](=[O:26])[CH3:25])(=O)C>C([O-])(=O)C.[Na+].C(OCC)(=O)C>[C:2]([O:3][C@@H:2]1[C@H:4]([O:5][C:4](=[O:5])[CH3:6])[C@@H:6]([CH2:7][O:8][C:24](=[O:26])[CH3:25])[O:9][C@H:1]1[N:10]1[CH:11]=[N:12][C:13]2[C:19]1=[N:18][CH:17]=[N:16][C:14]=2[OH:15])(=[O:3])[CH3:1]

Participants

5

Reactant 2

HCID 7918Acetic AnhydrideHCID 178521066(2R,3S,4R,5R)-2-(hydroxymethyl)-5-(6-hydroxypurin-9-yl)oxolane-3,4-diol

Product 1

HCID 178476357[(2R,3R,4R,5R)-3,4-diacetyloxy-5-(6-oxo-3H-purin-9-yl)oxolan-2-yl]methyl acetateYield 181.6%

Reagents, catalysts & solvents 2

HCID 517045Sodium AcetateCatalystHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
45 °C

Procedure

A suspension of 0.367 Kg (1.36 moles) of Inosine, 0.52 Kg (5.51 moles) of acetic anhydride and 5.6 g (0.068 mole) of sodium acetate is heated between 90° C. and 140° C. for about 4 hours. At the end of the reaction, the solids are dissolved. The reaction mixture is then cooled to about 45° C. and 0.75 L of ethyl acetate are added. The resulting suspension is stirred for about 1 hour at room temperature. The solid is filtered, washed with ethyl acetate and dried under reduced pressure at about 60° C. to afford 0.487 Kg of crude product. The crude product is used in the next reaction.

Workup

  1. temperatureis heated between 90° C. and 140° C. for about 4 hours
  2. customAt the end of the reaction
  3. dissolutionthe solids are dissolved
  4. filtrationThe solid is filtered
  5. washwashed with ethyl acetate
  6. customdried under reduced pressure at about 60° C.

Sources & evidence

ORD record
ord-9a1cabff512a402294ab0a476dbdb24c
Source dataset
uspto-grants-1991_02
Patent number
US04992535

Reaction notes

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