Toluene → N4-behenyloxy-1-beta-D-arabino-furanosylcytosine

HRID 1164148Notes

Reaction equation

HRID 1164148 reaction equation
[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.[K+].[CH2:30]([O:52]C(Cl)=O)[CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH2:47][CH2:48][CH2:49][CH2:50][CH3:51]>CC(N(C)C)=O.C(Cl)(Cl)Cl.CO>[CH2:30]([O:52][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)[CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH2:47][CH2:48][CH2:49][CH2:50][CH3:51]

Participants

7

Reactant 4

HCID 1140TolueneHCID 1146822(1H)-Pyrimidinone, 4-amino-1-arabinofuranosyl-HCID 516893Potassium BicarbonateHCID 10715346Carbonochloridic acid, docosyl ester

Product 1

HCID 22822390N4-behenyloxy-1-beta-D-arabino-furanosylcytosineYield 35.3%

Reagents, catalysts & solvents 2

HCID 31374DimethylacetamideSolventHCID 21584188Chloroform methanolSolvent

Procedure

to a solution of 2.43 g of arabinofuranosylcytosine dissolved in 40 ml of dimethylacetamide, there is added 10 ml of a toluene solution containing 3.0 g of potassium hydrogen carbonate and 5.8 g of behenyloxycarbonyl chloride. The reaction is carried out at room temperature with stirring of the mixture for 4 hours. After completion of the reaction, the mixture is poured into ice-water and the precipitated solids are collected by filtration, followed by washing successively with acetone and with chloroform. The white solids obtained are dissolved in a mixture of chloroform-methanol and the resultant insolubles are filtered off. After removal of the solvent, the rersidue is subjected to precipitation from chloroform to obtain 2.0 g of N4 -behenyloxy-1-β-D-arabino-furanosylcytosine (Yield:35%).

Workup

  1. customis carried out at room temperature
  2. customAfter completion of the reaction
  3. filtrationthe precipitated solids are collected by filtration
  4. washby washing successively with acetone and with chloroform
  5. customThe white solids obtained
  6. filtrationthe resultant insolubles are filtered off
  7. customAfter removal of the solvent
  8. customthe rersidue is subjected to precipitation from chloroform

Sources & evidence

ORD record
ord-6b1d546c0eee4f5e84a233e991aa0c93
Source dataset
uspto-grants-1983_01
Patent number
US04367332

Reaction notes

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