Famciclovir → Desacetyl Famciclovir

HRID 5868

Reaktionsgleichung

Reaktionsgleichung von HRID 5868
[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]

Komponenten

5

Edukt 2

HCID 3324FamciclovirHCID 11430Potassium Carbonate

Produkt 1

HCID 10039252Desacetyl FamciclovirAusbeute 30 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 176Acetic AcidKatalysatorHCID 887MethanolLösungsmittel

Versuchsvorschrift

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).

Aufarbeitung

  1. filtrationthe solution was filtered
  2. customthe solvent was removed
  3. customThe residue was purified by column chromatography on silica gel eluting with chloroform-methanol (15:1, 10:1)

Quellen und Nachweise

ORD-Eintrag
ord-46661896143e47e7a8d7bd3da3304edb
Quelldatensatz
uspto-grants-1993_09
Patentnummer
US05246937

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