Famciclovir → Desacetyl Famciclovir

HRID 5868

반응식

HRID 5868 반응식
[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]

참가 물질

5

반응물 2

HCID 3324FamciclovirHCID 11430Potassium Carbonate

생성물 1

HCID 10039252Desacetyl Famciclovir수율 30%

시약·촉매·용매 2

HCID 176Acetic Acid촉매HCID 887Methanol용매

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-46661896143e47e7a8d7bd3da3304edb
출처 데이터셋
uspto-grants-1993_09
특허 번호
US05246937

연결된 노트

불러오는 중…