Uridine, 2',3'-dideoxy-5-ethyl-3'-iodo- → 5-Et-ddU

HRID 232360Notes

Reaction equation

HRID 232360 reaction equation
[CH2:1]([C:3]1[C:4](=[O:18])[NH:5][C:6](=[O:17])[N:7]([CH:16]=1)[C@@H:8]1[O:14][C@H:11]([CH2:12][OH:13])[C@@H:10](I)[CH2:9]1)[CH3:2]>N.O.[Pd]>[CH2:1]([C:3]1[C:4](=[O:18])[NH:5][C:6](=[O:17])[N:7]([CH:16]=1)[C@@H:8]1[O:14][C@H:11]([CH2:12][OH:13])[CH2:10][CH2:9]1)[CH3:2]

Participants

5

Reactant 1

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

Product 1

HCID 4514525-Et-ddUYield 71.3%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 222AmmoniaSolventHCID 962WaterSolvent

Procedure

A solution of 2.50 g of 2',3'-dideoxy-5-ethyl-3'-iodouridine in a mixture of 90 ml of ethanolic ammonia and 17 ml of water was hydrogenated over 5% palladium on barium sulfate catalyst at room temperature and under atmospheric pressure for 3 hours. The mixture was filtered and the filtrate was evaporated. The residue was extracted twice with 250 ml of hot ethyl acetate each time and the combined ethyl acetate extracts were evaporated. The residue was chromatographed on a short column of silica gel using ethyl acetate for the elution and the product was crystallized from a mixture of ethyl acetate and hexane to give 1.17 g of 2',3'-dideoxy-5-ethyluridine in the form of a white solid of melting point 109°-113° C.

Workup

  1. filtrationThe mixture was filtered
  2. customthe filtrate was evaporated
  3. extractionThe residue was extracted twice with 250 ml of hot ethyl acetate each time
  4. customthe combined ethyl acetate extracts were evaporated
  5. customThe residue was chromatographed on a short column of silica gel
  6. washfor the elution
  7. customthe product was crystallized from a mixture of ethyl acetate and hexane

Sources & evidence

ORD record
ord-242e581e95754b6f8fb4fa6b1829b13a
Source dataset
uspto-grants-1989_07
Patent number
US04851519

Reaction notes

Loading…