HCID 14444213, compound → Uridine, 2',3'-dideoxy-5-ethyl-3'-iodo-

HRID 232359Notes

Reaction equation

HRID 232359 reaction equation
[CH2:1]([C:3]1[C:4](=[O:37])[NH:5][C:6](=[O:36])[N:7]([CH:35]=1)[C@@H:8]1[O:33][C@H:11]([CH2:12][O:13]C(C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[C@@H:10]([I:34])[CH2:9]1)[CH3:2]>C(O)(=O)C.O>[CH2:1]([C:3]1[C:4](=[O:37])[NH:5][C:6](=[O:36])[N:7]([CH:35]=1)[C@@H:8]1[O:33][C@H:11]([CH2:12][OH:13])[C@@H:10]([I:34])[CH2:9]1)[CH3:2]

Participants

4

Reactant 1

HCID 14444213HCID 14444213, compound

Product 1

HCID 451824Uridine, 2',3'-dideoxy-5-ethyl-3'-iodo-Yield 41.5%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Procedure

A solution of 720 mg of 2',3'-dideoxy-5-ethyl-3'-iodo-5'-O-trityluridine in a mixture of 16 ml of acetic acid and 4 ml of water was stirred and heated under reflux for 1 hour. The solvent was removed by evaporation and the residue was crystallized from a mixture of ethyl acetate and hexane to give 180 mg of 2',3'-dideoxy-5-ethyl-3'-iodouridine in the form of a white solid of melting point 161.5°-163° C.

Workup

  1. temperatureheated
  2. temperatureunder reflux for 1 hour
  3. customThe solvent was removed by evaporation
  4. customthe residue was crystallized from a mixture of ethyl acetate and hexane

Sources & evidence

ORD record
ord-1fca7ace5f67435bad437c2334184490
Source dataset
uspto-grants-1989_07
Patent number
US04851519

Reaction notes

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