Carbon tetrabromide → HCID 18633462, compound

HRID 232354Notes

Reaction equation

HRID 232354 reaction equation
[CH2:1]([O:3][C@@H:4]1[C@@H:8]([CH2:9]O)[O:7][C@@H:6]([N:11]2[CH:18]=[C:17]([CH2:19][CH3:20])[C:15](=[O:16])[NH:14][C:12]2=[O:13])[CH2:5]1)[CH3:2].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[N-:40]=[N+:41]=[N-:42].[Na+].C(Br)(Br)(Br)Br>CN(C)C=O.CO>[N:40]([CH2:9][C@H:8]1[O:7][C@@H:6]([N:11]2[CH:18]=[C:17]([CH2:19][CH3:20])[C:15](=[O:16])[NH:14][C:12]2=[O:13])[CH2:5][C@@H:4]1[O:3][CH2:1][CH3:2])=[N+:41]=[N-:42]

Participants

7

Reactant 4

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 33557Sodium AzideHCID 18633447HCID 18633447, compound

Product 1

HCID 18633462HCID 18633462, compoundYield 82.7%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6228DimethylformamideSolvent

Procedure

A mixture of 1.40 g of 2'-deoxy-3'-O-ethyl-5-ethyluridine, 1.3 g of triphenylphosphine, 1.59 g of sodium azide and 1.66 g of carbon tetrabromide in 19 ml of dimethylformamide was stirred at room temperature for 20 hours. 11 ml of methanol were added, the mixture was stirred for 30 minutes and then evaporated. The residue was suspended in 110 ml of water and extracted three times with 70 ml of ethyl acetate each time. The combined ethyl acetate extracts were evaporated and the residue was subject to flash chromatography on a column of silica gel using ethyl acetate/hexane (2:1) for the elution, there being obtained 1.26 g of 5'-azido-2',5'-dideoxy-3'-O-ethyl-5-ethyluridine in the form of a colorless oil.

Workup

  1. stirringthe mixture was stirred for 30 minutes
  2. customevaporated
  3. extractionextracted three times with 70 ml of ethyl acetate each time
  4. customThe combined ethyl acetate extracts were evaporated
  5. washfor the elution, there

Sources & evidence

ORD record
ord-1ea21f631de14826b29c956295990c22
Source dataset
uspto-grants-1989_07
Patent number
US04851519

Reaction notes

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