Carbon tetrabromide → HCID 18633462, compound

HRID 1085524Notes

Reaction equation

HRID 1085524 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-2fdd528a4a44408186e36ec6e483e9fe
Source dataset
uspto-grants-1991_04
Patent number
US05010060

Reaction notes

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