Carbon tetrabromide → HCID 53878961, compound

HRID 232381Notes

Reaction equation

HRID 232381 reaction equation
[CH2:1]([C:3]1[C:4](=[O:20])[NH:5][C:6](=[O:19])[N:7]([CH:18]=1)[C@@H:8]1[O:17][C@H:12]([CH2:13][CH2:14][CH2:15]O)[C@@H:10]([OH:11])[CH2:9]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>[N:40]([CH2:15][CH2:14][CH2:13][C@H:12]1[O:17][C@@H:8]([N:7]2[CH:18]=[C:3]([CH2:1][CH3:2])[C:4](=[O:20])[NH:5][C:6]2=[O:19])[CH2:9][C@@H:10]1[OH:11])=[N+:41]=[N-:42]

Participants

6

Reactant 4

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 33557Sodium AzideHCID 53671578HCID 53671578, compound

Product 1

HCID 53878961HCID 53878961, compoundYield 20.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 1.25 g of 2',5'-dideoxy-5-ethyl-5'-(2-hydroxyethyl)uridine, 1.18 g of triphenylphosphine, 1.49 g of sodium azide and 1.55 g of carbon tetrabromide in 30 ml of dimethylformamide was stirred at room temperature overnight. The mixture was evaporated to dryness and the residue was partitioned between ethyl acetate and water. The ethyl acetate solution was evaporated to dryness and the residue was subjected to flash chromatography on a column of silica gel using 1% methanol/dichloromethane for the elution to give 0.28 g of 5'-(2-azidoethyl)-2',5'-dideoxy-5-ethyluridine in the form of a colorless oil which crystallized upon standing.

Workup

  1. customThe mixture was evaporated to dryness
  2. customthe residue was partitioned between ethyl acetate and water
  3. customThe ethyl acetate solution was evaporated to dryness
  4. washthe residue was subjected to flash chromatography on a column of silica gel using 1% methanol/dichloromethane for the elution

Sources & evidence

ORD record
ord-ed2c43d449444bba80c76cd5d41cfb58
Source dataset
uspto-grants-1989_07
Patent number
US04851519

Reaction notes

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