1-Methylimidazole → Zidovudine

HRID 2081964Notes

Reaction equation

HRID 2081964 reaction equation
[CH3:1][C:2]1[C:8](=[O:9])[NH:7][C:5](=[O:6])[N:4]([C@@H:10]2[O:14][C@H:13]([CH2:15][OH:16])[C@@H:12]([N:17]=[N+:18]=[N-:19])[CH2:11]2)[CH:3]=1.C(CCOP([O-])([O-])=O)#N.[C@@H]1(N2C3N=CN=C(N)C=3N=C2)O[C@H](CO)CC1.C(C1C=C(C(C)C)C=C(C(C)C)C=1S(Cl)(=O)=O)(C)C.CN1C=CN=C1>N1C=CC=CC=1>[CH3:1][C:2]1[C:8](=[O:9])[NH:7][C:5](=[O:6])[N:4]([C@@H:10]2[O:14][C@H:13]([CH2:15][OH:16])[C@@H:12]([N:17]=[N+:18]=[N-:19])[CH2:11]2)[CH:3]=1

Participants

6

Reactant 4

HCID 13901-MethylimidazoleHCID 20039DideoxyadenosineHCID 810422,4,6-Tris(1-methylethyl)benzenesulfonyl chlorideHCID 86746554AZT cyanoethylphosphate

Product 1

HCID 35370Zidovudine

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

AZT cyanoethylphosphate (600 mg, 1.5 mmol) and 2',3'-dideoxyadenosine (352 mg, 1.5 mmol) were dissolved in 60 ml of distilled pyridine. To the solution, 1.21 g (4 mmol) of 2,4,6-triisopropylbenzenesulfonyl chloride was added and stirred for 30 min., following by adding 0.984 ml (12 mmol) of N-methylimidazole and stirring at room temperature for 18 hours in a sealed flask, yielding AZT-DDA cyanoethylphosphate triester in solution.

Workup

  1. stirringstirring at room temperature for 18 hours in a sealed flask

Sources & evidence

ORD record
ord-1466ce97b5a54f139d1e341734863015
Source dataset
uspto-grants-1993_02
Patent number
US05187163

Reaction notes

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