Cytidine → Cytarabine

HRID 1605213Notes

Reaction equation

HRID 1605213 reaction equation
[C@@H:1]1([N:10]2[CH:17]=[CH:16][C:14]([NH2:15])=[N:13][C:11]2=[O:12])[O:9][C@H:6]([CH2:7][OH:8])[C@@H:4]([OH:5])[C@H:2]1[OH:3].C([O-])(=O)C.C([O-])(=O)C.C([O-])(=O)C.C([O-])(=O)C.[Si+4]>C(O)(=O)C>[C@@H:1]1([N:10]2[CH:17]=[CH:16][C:14]([NH2:15])=[N:13][C:11]2=[O:12])[O:9][C@H:6]([CH2:7][OH:8])[C@@H:4]([OH:5])[C@@H:2]1[OH:3]

Participants

4

Reactant 2

HCID 6175CytidineHCID 20057181HCID 20057181, compound

Product 1

HCID 6253CytarabineYield 50%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
120 °C

Procedure

1.0 G of cytidine is dissolved in 20 ml of acetic acid under heating. After cooling, 2.17 g of silicon tetraacetate are added to the solution. The mixture is stirred at 120°C for 5 minutes. The mixture is cooled to room temperature, and 0.6 ml of boron trifluoride-ether complex is added thereto. Then, the mixture is stirred at room temperature for 4 days. After the reaction, the mixture is concentrated under reduced pressure, and the residue is treated in the same manner as described in Example 3. 0.5 g of 1-β-D-arabinofuranosyl cytosine is thereby obtained. Yield: 50 % M.p. 213°-214°C (decomp.) (recrystallized from 50 % ethanol)

Workup

  1. temperatureunder heating
  2. temperatureAfter cooling
  3. temperatureThe mixture is cooled to room temperature
  4. addition0.6 ml of boron trifluoride-ether complex is added
  5. stirringThen, the mixture is stirred at room temperature for 4 days
  6. customAfter the reaction
  7. concentrationthe mixture is concentrated under reduced pressure
  8. additionthe residue is treated in the same manner

Sources & evidence

ORD record
ord-5570cedc4fff4aa688d2b2a9f5be0679
Source dataset
uspto-grants-1976_04
Patent number
US03950325

Reaction notes

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