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

HRID 1164146Notes

Reaction equation

HRID 1164146 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.[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]

Participants

6

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Procedure

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%).

Workup

  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

Sources & evidence

ORD record
ord-1a4b8043bfa3411c81e2b8358b178cef
Source dataset
uspto-grants-1983_01
Patent number
US04367332

Reaction notes

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