Water → Stavudine

HRID 913261

Reaction equation

HRID 913261 reaction equation
S(O[C@@H:6]1[C@@H:10]([CH2:11][O:12]S(C)(=O)=O)[O:9][C@@H:8]([N:17]2[CH:25]=[C:23]([CH3:24])[C:21](=[O:22])[NH:20][C:18]2=[O:19])[CH2:7]1)(C)(=O)=O.[OH-].[Na+].O.CC(C)([O-])C.[K+]>CS(C)=O>[CH3:24][C:23]1[C:21](=[O:22])[NH:20][C:18](=[O:19])[N:17]([C@@H:8]2[O:9][C@H:10]([CH2:11][OH:12])[CH:6]=[CH:7]2)[CH:25]=1

Participants

6

Reactant 4

HCID 962WaterHCID 14798Sodium HydroxideHCID 10572932HCID 10572932, compoundHCID 23665647Potassium tert-butoxide

Product 1

HCID 18283StavudineYield 79%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

In the above synthesis, 3′,5′-di-O-mesylthymidine is first treated with sodium hydroxide in refluxing water for 2 hours and the resultant 3,4-anhydrothymidine is treated with potassium t-butoxide in dimethyl sulfoxide (DMSO) at room temperature for 2 hrs. The reaction mixture is neutralized, evaporated to dryness and after a series of manipulations which included extraction, declourization, precipitation and recrystallization, gave Stavudine in 79% yield and an overall yield of 56%.

Workup

  1. customevaporated to dryness
  2. extractionextraction, declourization, precipitation and recrystallization

Sources & evidence

ORD record
ord-b60f983729914b91a099b1bb67103bf9
Source dataset
uspto-grants-2011_09
Patent number
US08026356B2

Linked notes

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