Diacetylacyclovir → Acyclovir

HRID 865356Notes

Reaction equation

HRID 865356 reaction equation
C([O:4][CH2:5][CH2:6][O:7][CH2:8][N:9]1[CH:17]=[N:16][C:15]2[C:14](=[O:18])[NH:13][C:12]([NH:19]C(=O)C)=[N:11][C:10]1=2)(=O)C>CO.[OH-].[NH4+]>[OH:4][CH2:5][CH2:6][O:7][CH2:8][N:9]1[CH:17]=[N:16][C:15]2[C:14](=[O:18])[NH:13][C:12]([NH2:19])=[N:11][C:10]1=2

Participants

4

Reactant 1

HCID 135433881Diacetylacyclovir

Product 1

HCID 135398513AcyclovirYield 90%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 14923Ammonium HydroxideSolvent

Procedure

9-(2-Acetoxyethoxy)methyl-N2 -acetylguanine (1.3 gm, 4.2 mmol) was dissolved in 10 ml of methanol and 10 ml of concentrated ammonium hydroxide, and the solution was heated at 50° C. for a period of 4 hours. The solvents were evaporated off, yielding a solid. The solid was recrystallized from methanol, yielding 0.85 gm of 9-(2-hydroxyethoxy)methylguanine (90% yield). Characteristic analytical data are as follows: 1H NMR(DMSO-d6), δ3.16 (4H, singlet, --OCH2CH2O--), 4.6 (1H, br singlet, --OH), 5.26 (2H, singlet, --NCH2 --), 6.45 (2H, br singlet, --NH2), 7.76 (1H, singlet, --N=CH--N--).

Workup

  1. customThe solvents were evaporated off
  2. customyielding a solid
  3. customThe solid was recrystallized from methanol

Sources & evidence

ORD record
ord-8c8f7c740914429dbac7e72556d95a05
Source dataset
uspto-grants-1996_10
Patent number
US05565565

Reaction notes

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