Sodium Acetate → Acyclovir

HRID 1440013Notes

Reaction equation

C([O-])(=O)C.[Na+].[Na].C([O:10][CH2:11][CH2:12][O:13][CH2:14][N:15]1[CH:23]=[N:22][C:21]2[C:20](=[O:24])[NH:19][C:18]([NH2:25])=[N:17][C:16]1=2)(=O)C>>[OH:10][CH2:11][CH2:12][O:13][CH2:14][N:15]1[CH:23]=[N:22][C:21]2[C:20](=[O:24])[NH:19][C:18]([NH2:25])=[N:17][C:16]1=2

Participants

Reactant 3

HCID 517045Sodium Acetate

HCID 5360545Sodium

HCID 1354469309-(2-Acetoxyethoxymethyl)guanine

Product 1

HCID 135398513Acyclovir

Procedure

A process for the synthesis of 9-(2-hydroxyethoxy methyl) guanine, comprising reacting guanine, or a salt thereof with between 2 and 4 moles of hexamethyldisilazane, in the presence of an aprotic solvent and of a catalytic amount of ammonium sulphate; reacting the resulting guanine trimethylsilyl derivative, without being isolated, with a stoichiometric quantity of acyloxyethoxy methyl halide at a temperature of 50° to 100° C.; and hydrolyzing with a sodium acetate or sodium hydroxyde water solution the resulting 9-(2-acetoxyethoxy methyl) guanine, to provide 9-(2-hydroxyethoxy methyl) guanine.

Sources & evidence

ORD record: ord-06aadb4eb48f4ff38cca468048f2905b
Source dataset: uspto-grants-1996_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05496945

Reaction notes

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