Triethylamine → N4-butyloxycarbonyl-1-beta-D-arabinofuranosylcytosine

HRID 1164142

반응식

HRID 1164142 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].C(N(CC)CC)C.[CH2:25]([O:29][C:30](Cl)=[O:31])[CH2:26][CH2:27][CH3:28]>CC(N(C)C)=O.C(O)C>[CH2:25]([O:29][C:30]([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:31])[CH2:26][CH2:27][CH3:28]

참가 물질

6

반응물 3

HCID 8471TriethylamineHCID 61140Butyl chloroformateHCID 1146822(1H)-Pyrimidinone, 4-amino-1-arabinofuranosyl-

생성물 1

HCID 13090270N4-butyloxycarbonyl-1-beta-D-arabinofuranosylcytosine수율 50%

시약·촉매·용매 2

HCID 702Ethanol용매HCID 31374Dimethylacetamide용매

실험 절차

To a solution of 4.0 g of arabinofuranosylcytosine dissolved in 50 ml of dimethylacetamide, there are added 5.0 g of triethylamine and 3.37 g of butyloxycarbonyl chloride. The reaction is carried out by stirring the mixture at room temperature for 3 hours. After completion of the reaction, the solvent is evaoprated under reduced pressure. The residue is diluted with 20 ml of ethanol, followed by addition of 150 ml of petroleum ether. After the mixture is stirred at 0° to 5° C. for one hour, the resultant precipitates are collected by filtration. The precipitates are dissolved in 15 ml of methanol and then 100 ml of water is added to the resultant solution. The mixture is left to stand in a refrigerator and the precipitated crystals are filtered to give 2.8 g of N4 -butyloxycarbonyl-1-β-D-arabinofuranosylcytosine (Yield:50%).

후처리

  1. customAfter completion of the reaction
  2. stirringAfter the mixture is stirred at 0° to 5° C. for one hour
  3. customthe resultant precipitates
  4. filtrationare collected by filtration
  5. dissolutionThe precipitates are dissolved in 15 ml of methanol
  6. addition100 ml of water is added to the resultant solution
  7. waitThe mixture is left
  8. filtrationthe precipitated crystals are filtered

출처 및 근거

ORD 기록
ord-d7ea7f7b48384afca8aa126ee48a750b
출처 데이터셋
uspto-grants-1983_01
특허 번호
US04367332

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