Toluene → N4-undecyloxycarbonyl-1-beta-D-arabinofuranosylcytosine

HRID 1164146

反応式

HRID 1164146 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].C1(C)C=CC=CC=1.C(=O)([O-])O.[Na+].[CH2:30]([O:41][C:42](Cl)=[O:43])[CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH3:40]>CC(N(C)C)=O>[CH2:30]([O:41][C:42]([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:43])[CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH3:40]

参加物

6

反応物 4

HCID 1140TolueneHCID 1146822(1H)-Pyrimidinone, 4-amino-1-arabinofuranosyl-HCID 516892Sodium BicarbonateHCID 20513604Undecyloxycarbonyl chloride

生成物 1

HCID 13090287N4-undecyloxycarbonyl-1-beta-D-arabinofuranosylcytosine収率 30.4%

試薬・触媒・溶媒 1

HCID 31374Dimethylacetamide溶媒

実験手順

In 130 ml of dimethylacetamide, 7.3 g of arabinofuranosylcytosine is dissolved and to the resultant solution is added 40 ml of a toluene solution containing 7.56 g of sodium hydrogen carbonate and 7.0 g of undecyloxycarbonyl chloride. The mixture is then stirred at room temperature for 3 hours. After the reaction is over, the solvent is removed under reduced pressure and ice-water is added to the residue, whereby the cyrstals are precipitated. The crystals are filtered and washed with water, followed by sufficient drying. Recrystallization of the product is performed twice, using 80 ml of chloroform-n-hexane, to give 4.0 g of N4-undecyloxycarbonyl-1-β-D-arabinofuranosylcytosine (Yield:30%).

後処理

  1. customis removed under reduced pressure and ice-water
  2. additionis added to the residue, whereby the cyrstals
  3. customare precipitated
  4. filtrationThe crystals are filtered
  5. washwashed with water
  6. customRecrystallization of the product

出典と根拠

ORDレコード
ord-1a4b8043bfa3411c81e2b8358b178cef
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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