Sodium Azide → Zidovudine

HRID 1885526Notes

Reaction equation

HRID 1885526 reaction equation
[CH3:1][C:2]1[C:15](=[O:16])[N:14]=[C:13]2[N:4]([C@@H:5]3[O:9][C@H:8]([CH2:10][OH:11])[C@@H:7]([O:12]2)[CH2:6]3)[CH:3]=1.[N-:17]=[N+:18]=[N-:19].[Na+]>CN(C=O)C.O>[N:17]([C@@H:7]1[C@@H:8]([CH2:10][OH:11])[O:9][C@@H:5]([N:4]2[CH:3]=[C:2]([CH3:1])[C:15](=[O:16])[NH:14][C:13]2=[O:12])[CH2:6]1)=[N+:18]=[N-:19]

Participants

5

Reactant 2

HCID 33557Sodium AzideHCID 69157522,3'-Anhydrothymidine

Product 1

HCID 35370Zidovudine

Reagents, catalysts & solvents 2

HCID 962WaterSolvent3×HCID 6228DimethylformamideSolvent

Procedure

2,3'-Anhydrothymidine (25 O: 0.1115 mol) and NaN3 (29 g, 0.446 mol) was suspended in a mixture of 250 ml DMF and 38 ml H2O. The reaction was refluxed for 5 hours at which time it was poured into 1 liter of H2O. The aqueous solution was extracted with EtOAc (3×700 ml). The EtOAc was dried over Na2SO4, filtered and the EtOAoac was removed in vacuo to yield a viscous oil. This oil was stirred with 200 ml water resulting in a solid 9.15 g (0.0342 mol, 30.7%). mp=116°-118° C.

Workup

  1. temperatureThe reaction was refluxed for 5 hours at which time it
  2. extractionThe aqueous solution was extracted with EtOAc (3×700 ml)
  3. dry with materialThe EtOAc was dried over Na2SO4
  4. filtrationfiltered
  5. customthe EtOAoac was removed in vacuo
  6. customto yield a viscous oil

Sources & evidence

ORD record
ord-2d344eeb444d49d78bd0a885285547e1
Source dataset
uspto-grants-1992_09
Patent number
US05145840

Reaction notes

Loading…