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

HRID 1164146

반응식

HRID 1164146 반응식
[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]

참가 물질

6

반응물 4

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

생성물 1

HCID 13090287N4-undecyloxycarbonyl-1-beta-D-arabinofuranosylcytosine수율 30.4%

시약·촉매·용매 1

HCID 31374Dimethylacetamide용매

실험 절차

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%).

후처리

  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

출처 및 근거

ORD 기록
ord-1a4b8043bfa3411c81e2b8358b178cef
출처 데이터셋
uspto-grants-1983_01
특허 번호
US04367332

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