Famciclovir → Desacetyl Famciclovir

Reaction equation

[C:1]([O:4][CH2:5][CH:6]([CH2:19][O:20]C(=O)C)[CH2:7][CH2:8][N:9]1[CH:17]=[N:16][C:15]2[C:10]1=[N:11][C:12]([NH2:18])=[N:13][CH:14]=2)(=[O:3])[CH3:2].C(=O)([O-])[O-].[K+].[K+]>CO.C(O)(=O)C>[C:1]([O:4][CH2:5][CH:6]([CH2:19][OH:20])[CH2:7][CH2:8][N:9]1[CH:17]=[N:16][C:15]2[C:10]1=[N:11][C:12]([NH2:18])=[N:13][CH:14]=2)(=[O:3])[CH3:2]

Participants

Procedure

To a solution of 9-(4-acetoxy-3-acetoxymethylbut-1-yl)-2-aminopurine (0.48 g, 1.5 mmol) in methanol (9 ml) was added anhydrous potassium carbonate (14 mg, 0.1 mmol) and the solution was stirred for 20 minutes. Two drops of glacial acetic acid were added, the solution was filtered and the solvent was removed. The residue was purified by column chromatography on silica gel eluting with chloroform-methanol (15:1, 10:1) to afford 9-(4-acetoxy-3-hydroxymethylbut-1-yl)-2-aminopurine as a white crystalline solid (124 mg, 30%), m.p. 166°-168°; νmax (KBr) 3440, 3220, 1720, 1650, 1615, and 1580 cm-1 ; δH [(CD3)2SO]1.68 (1H, m, 3'-H), 1.82 (2H, m, 2'-H), 1.98 (3H, s, CH3), 3.41 (2H, t, J4.8 Hz, D2O exchange gives d, CH 2 OH), 3.9-4.05 (2H, AB part of ABX, JAB 10.9 Hz and JAX =JBX 5.8 Hz, CH2OCO), 4.12 (2H, t, J 7.2 Hz, 1'-H), 4.62 (1H, t, J 5.0 Hz, D2O exchangeable, OH), 6.44 (2H, s, D2O exchangeable, 2-NH2), 8.07 (1H, s, 8-H), and 8.56 (1H, s, 6-H); (Observed M+, 279.1326. C12H17N5O3 requires 279.1331).