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

HRID 1905000Notes

Reaction equation

HRID 1905000 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]>CCOCC>[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

3

Reactant 1

HCID 14444213HCID 14444213, compound

Product 1

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

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 5-ethyl-3'-Iodo-5'-O-trityl-2',3'-dideoxyuridine (1.73 g, 2.8 mmole) and 80% HAc (25 ml) is heated at 100° C. for 50 min. After heating, acetic acid is evacuated in vacuo to obtain an amorphous solid. Ether is added, the product is triturated, and the resulting yellowish solid is filtered for collection (350 mg). Another 250 mg is obtained from the filtrate after repeating the above procedure, m.p. 162°-164° C.

Workup

  1. temperatureAfter heating
  2. customacetic acid is evacuated in vacuo
  3. customto obtain an amorphous solid
  4. customthe product is triturated
  5. filtrationthe resulting yellowish solid is filtered for collection (350 mg)
  6. customAnother 250 mg is obtained from the filtrate

Sources & evidence

ORD record
ord-90564aff148c4205a51bc33222460dcd
Source dataset
uspto-grants-1989_06
Patent number
US04841039

Reaction notes

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