Toluene → N4-palmityloxycarbonylarabinofuranosylcytosine

HRID 1164147

Reaction equation

HRID 1164147 reaction equation
C1(C)C=CC=CC=1.[CH2:8]([O:24][C:25](Cl)=[O:26])[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH3:23].[CH:28]1([N:37]2[CH:44]=[CH:43][C:41]([NH2:42])=[N:40][C:38]2=[O:39])[O:34][C@H:33]([CH2:35][OH:36])[C@@H:31]([OH:32])[C@@H:29]1[OH:30].C(=O)([O-])O.[Na+]>CC(N(C)C)=O>[CH2:8]([O:24][C:25]([NH:42][C:41]1[CH:43]=[CH:44][N:37]([CH:28]2[O:34][C@H:33]([CH2:35][OH:36])[C@@H:31]([OH:32])[C@@H:29]2[OH:30])[C:38](=[O:39])[N:40]=1)=[O:26])[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH3:23]

Participants

6

Reactant 4

HCID 1140TolueneHCID 97633Cetyl chloroformateHCID 1146822(1H)-Pyrimidinone, 4-amino-1-arabinofuranosyl-HCID 516892Sodium Bicarbonate

Product 1

HCID 86738731N4-palmityloxycarbonylarabinofuranosylcytosineYield 30.5%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Procedure

A toluene solution containing 1.8 g of palmityloxycarbonyl chloride is added to 20 ml of a dimethylacetamide solution containing 1.5 g of arabinofuranosylcytosine and 1.7 g of sodium hydrogen carbonate. The reaction is carried out at room temperature with stirring of the mixture for 3 hours. After the reaction is completed, the reaction mixture is poured into an ice-water and the precipitated solids are collected by filtration, followed by washing successively with acetone and with hot chloroform. The resultant solids are dissolved in a mixture of chloroform-methanol and then subjected once to filtration, followed by removal of the solvent. The residue is subjected to crystallization from n-hexane to give 0.92 g of N4 -palmityloxycarbonylarabinofuranosylcytosine (Yield:30%).

Workup

  1. customis carried out at room temperature
  2. filtrationthe precipitated solids are collected by filtration
  3. washby washing successively with acetone and with hot chloroform
  4. dissolutionThe resultant solids are dissolved in a mixture of chloroform-methanol
  5. filtrationsubjected once to filtration
  6. customfollowed by removal of the solvent
  7. customThe residue is subjected to crystallization from n-hexane

Sources & evidence

ORD record
ord-c831318232c74dc18a76d840e18e0fb7
Source dataset
uspto-grants-1983_01
Patent number
US04367332

Linked notes

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