Sodium periodate → HCID 135707812, compound

HRID 845034Notes

Reaction equation

HRID 845034 reaction equation
I([O-])(=O)(=O)=O.[Na+].[OH:7][CH:8](CO)[CH2:9][O:10][CH2:11][N:12]1[CH:20]=[N:19][C:18]2[C:17](=[O:21])[NH:16][C:15]([NH2:22])=[N:14][C:13]1=2>O>[NH:16]1[C:17](=[O:21])[C:18]2[N:19]=[CH:20][N:12]([CH2:11][O:10][CH2:9][CH:8]=[O:7])[C:13]=2[N:14]=[C:15]1[NH2:22]

Participants

4

Reactant 2

HCID 23667635Sodium periodateHCID 135446919Iso Ganciclovir

Product 1

HCID 135707812HCID 135707812, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a vigorously stirred solution of 1.42 g (6.66 mmole) of sodium periodate in 14 ml of water at room temperature was added 1.34 g (5 mmole) of 9-(2,3-dihydroxy-1-propoxymethyl)guanine. The addition was accompanied by a mild exotherm. The reaction flask was stoppered, and stirring was continued at ambient temperature. After 1.5 hours, by which time the reaction was judged to be complete by high pressure liquid chromatography, the mixture was filtered. The solid on the filter was washed with small volumes of cold water and then with acetone. After air-drying overnight, yield of white powder was 1.13 g (90%), m.p. 350° (darkened beginning at about 250° without melting). Satisfactory purity was confirmed by TLC (80:20:2 CHCl3 -methanol-H2O) and analytical high pressure liquid chromatography (H2O, C8 reverse phase). By NMR (DMSO-d6) the material existed as a mixture of free aldehyde and covalent hydrate in a ratio of approximately 1:3 (This ratio was variable in different preparations).

Workup

  1. additionThe addition
  2. customwas continued at ambient temperature
  3. filtrationthe mixture was filtered
  4. washThe solid on the filter was washed with small volumes of cold water
  5. customAfter air-drying overnight
  6. custom1.13 g (90%), m.p. 350° (darkened beginning at about 250° without melting)
  7. additionBy NMR (DMSO-d6) the material existed as a mixture of free aldehyde and covalent hydrate in a ratio of approximately 1:3 (This ratio

Sources & evidence

ORD record
ord-59c624723aef44a0a2a42d24213f628f
Source dataset
uspto-grants-1988_07
Patent number
US04755516

Reaction notes

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