Carbon tetrabromide → HCID 18608979, compound

HRID 232361Notes

Reaction equation

HRID 232361 reaction equation
[CH2:1]([C:3]1[C:4](=[O:17])[NH:5][C:6](=[O:16])[N:7]([CH:15]=1)[C@@H:8]1[O:14][C@H:11]([CH2:12]O)[CH2:10][CH2:9]1)[CH3:2].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[N-:37]=[N+:38]=[N-:39].[Na+].C(Br)(Br)(Br)Br>CO>[N:37]([CH2:12][C@H:11]1[O:14][C@@H:8]([N:7]2[CH:15]=[C:3]([CH2:1][CH3:2])[C:4](=[O:17])[NH:5][C:6]2=[O:16])[CH2:9][CH2:10]1)=[N+:38]=[N-:39]

Participants

6

Reactant 4

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 33557Sodium AzideHCID 4514525-Et-ddU

Product 1

HCID 18608979HCID 18608979, compoundYield 51.8%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 350 mg of 2',3'-dideoxy-5-ethyluridine, 391 mg of triphenylphosphine, 475 mg of sodium azide and 496 mg of carbon tetrabromide was stirred at room temperature for 20 hours. 3 ml of methanol were added, the mixture was stirred for 1 hour and then evaporated. The residue was suspended in 30 ml of water and extracted twice with 50 ml of ethyl acetate each time. The combined ethyl acetate extracts were washed with 20 ml of water and then evaporated. The residue was subjected to flash chromatography on a column of silica gel using ethyl acetate for the elution. The product was crystallized from a mixture of ethyl acetate and hexane to give 200 mg of 5'-azido-2',3',5'-trideoxy-5-ethyluridine in the form of a white solid which was processed directly without further purification.

Workup

  1. stirringthe mixture was stirred for 1 hour
  2. customevaporated
  3. extractionextracted twice with 50 ml of ethyl acetate each time
  4. washThe combined ethyl acetate extracts were washed with 20 ml of water
  5. customevaporated
  6. washfor the elution
  7. customThe product was crystallized from a mixture of ethyl acetate and hexane

Sources & evidence

ORD record
ord-453613ff9a6341bbaea442a6dd1c8d27
Source dataset
uspto-grants-1989_07
Patent number
US04851519

Reaction notes

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