Pyridine → 4-Acetoxy-3-(acetoxymethyl)but-1-yl-2-aminopurine

HRID 273281

反応式

HRID 273281 の反応式
[NH2:1][C:2]1[N:10]=[C:9]2[C:5]([N:6]=CN2CCC(CO)CO)=[CH:4][N:3]=1.[N:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.[C:24]([O:27][C:28](=[O:30])[CH3:29])(=O)C>O1CCCC1.CN(C)C1C=CN=CC=1>[C:28]([O:30][C:9]12[N:18]=[C:23]([CH2:22][CH2:21][CH:20]([CH2:24][O:27][C:28](=[O:30])[CH3:29])[CH3:19])[N:6]=[C:5]1[CH:4]=[N:3][C:2]([NH2:1])=[N:10]2)(=[O:27])[CH3:29]

参加物

6

反応物 3

HCID 1049PyridineHCID 7918Acetic AnhydrideHCID 1285176-Deoxypenciclovir

生成物 1

HCID 866091624-Acetoxy-3-(acetoxymethyl)but-1-yl-2-aminopurine収率 75%

試薬・触媒・溶媒 2

HCID 142844-(Dimethylamino)pyridine触媒HCID 8028Tetrahydrofuran溶媒

実験手順

23.73 g (0.1 mole) of 2-amino-9-(4-hydroxy-3-(hydroxymethyl)but-1-yl)purine was suspended in 300 ml of tetrahydrofuran. To the suspension, 24.52 g (0.31 mole) of pyridine, 1.22 g (0.01 mole) of 4-dimethylaminopyridine and 21.44 g (0.21 mole) of acetic acid anhydride were added, and the mixture was stirred for five hours at room temperature. After completion of the reaction, the reaction product was concentrated under reduced pressure. The remaining concentrate was added to 300 ml of purified water and then extracted four times with 400 ml portions of chloroform. The organic layer was collected, and dried with anhydrous magnesium sulfate, followed by filtration and washing. The resulting filtrate was concentrated under reduced pressure and crystallized from butanol, thereby giving 24.10 g (75% yield) of white 9-[4-acetoxy-3-(acetoxymethyl)but-1-yl-2-aminopurine (famciclovir).

後処理

  1. customAfter completion of the reaction
  2. concentrationthe reaction product was concentrated under reduced pressure
  3. concentrationThe remaining concentrate
  4. additionwas added to 300 ml of purified water
  5. extractionextracted four times with 400 ml portions of chloroform
  6. customThe organic layer was collected
  7. dry with materialdried with anhydrous magnesium sulfate
  8. filtrationfollowed by filtration
  9. washwashing
  10. concentrationThe resulting filtrate was concentrated under reduced pressure
  11. customcrystallized from butanol

出典と根拠

ORDレコード
ord-ba39120c9555468b906f45ef3bc6df9b
出典データセット
uspto-grants-2008_11
特許番号
US07456282B2

関連ノート

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