Pyridine → HCID 22841937, compound

HRID 1461692Notes

Reaction equation

HRID 1461692 reaction equation
N1C=CC=CC=1.N([C@@H:10]1[C@@H:14]([CH2:15][OH:16])[O:13][C@@H:12]([N:17]2[CH:25]=[C:23]([CH3:24])[C:21](=[O:22])[NH:20][C:18]2=[O:19])[CH2:11]1)=[N+]=[N-].[C:26](OC(=O)C)(=[O:28])[CH3:27]>C(Cl)(Cl)Cl>[C:26]([O:16][CH2:15][C@H:14]1[O:13][C@@H:12]([N:17]2[CH:25]=[C:23]([CH3:24])[C:21](=[O:22])[NH:20][C:18]2=[O:19])[CH2:11][CH2:10]1)(=[O:28])[CH3:27]

Participants

5

Reactant 3

HCID 1049PyridineHCID 7918Acetic AnhydrideHCID 35370Zidovudine

Product 1

HCID 22841937HCID 22841937, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a pyridine (50 ml) solution of 3'-azido-3'-deoxythymidine (5.0 g, 18.7 mmole) 1 was added acetic anhydride dropwise in an ice-water bath. The mixture was allowed to stand overnight in the refrigerator. The solution was then poured into CHCl3 (20 ml), washed with H2O (200 ml×2), with a saturated solution of sodium bicarbonate and then H2O (200 ml×2). The organic layer was then dried (MgSO4). After removing the solvent, a syrup (6.5 g) was obtained.

Workup

  1. washwashed with H2O (200 ml×2), with a saturated solution of sodium bicarbonate
  2. dry with materialThe organic layer was then dried (MgSO4)
  3. customAfter removing the solvent

Sources & evidence

ORD record
ord-1ad77f26b9514d7d93d9fb0b928bda49
Source dataset
uspto-grants-1991_12
Patent number
US05077279

Reaction notes

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