2(1H)-Pyrimidinone, 4-amino-1-arabinofuranosyl- → N4-heptyloxycarbonyl-1-beta-D-arabinofuranosylcytosine

HRID 1164144

反応式

HRID 1164144 の反応式
[CH:1]1([N:10]2[CH:17]=[CH:16][C:14]([NH2:15])=[N:13][C:11]2=[O:12])[O:7][C@H:6]([CH2:8][OH:9])[C@@H:4]([OH:5])[C@@H:2]1[OH:3].C(=O)([O-])O.[Na+].[CH2:23]([O:30][C:31](Cl)=[O:32])[CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH3:29].C(Cl)(Cl)Cl.C(#N)C>CC(N(C)C)=O>[CH2:23]([O:30][C:31]([NH:15][C:14]1[CH:16]=[CH:17][N:10]([C@@H:1]2[O:7][C@H:6]([CH2:8][OH:9])[C@@H:4]([OH:5])[C@@H:2]2[OH:3])[C:11](=[O:12])[N:13]=1)=[O:32])[CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH3:29]

参加物

6

反応物 4

HCID 1146822(1H)-Pyrimidinone, 4-amino-1-arabinofuranosyl-HCID 118547Carbonochloridic acid, heptyl esterHCID 516892Sodium BicarbonateHCID 22555007Acetonitrile chloroform

生成物 1

HCID 13090280N4-heptyloxycarbonyl-1-beta-D-arabinofuranosylcytosine収率 40%

試薬・触媒・溶媒 1

HCID 31374Dimethylacetamide溶媒2 回

実験手順

To a solution of 4.0 g of arabinofuranosylcytosine dissolved in 50 ml of dimethylacetamide, there are added 4.15 g of sodium hydrogen carbonate and 4.41 g of heptylchloroformate. The resultant mixture is allowed to react under stirring at room temperature for 3 hours. After the reaction, dimethylacetamide is removed under reduced pressure and 150 ml of cold water is added to the residue. After the mixture is stirred for 2 hours, the solids are collected by filtration and dried. Recrystallization of the white powders obtained is performed twice, using 200 ml and 150 ml of a mixture of chloroform-acetonitrile (1:1), to give 2.5 g of N4 -heptyloxycarbonyl-1-β-D-arabinofuranosylcytosine (Yield:40%).

後処理

  1. customto react
  2. customis removed under reduced pressure and 150 ml of cold water
  3. additionis added to the residue
  4. stirringAfter the mixture is stirred for 2 hours
  5. filtrationthe solids are collected by filtration
  6. customdried
  7. customRecrystallization of the white powders
  8. customobtained

出典と根拠

ORDレコード
ord-4299755956584ea7881a35bdbfd2b279
出典データセット
uspto-grants-1983_01
特許番号
US04367332

関連ノート

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