Sodium Hydroxide → Stavudine

HRID 988751

Reaction equation

HRID 988751 reaction equation
S([CH:5]1[C@H:9](O)[C@@H:8]([CH2:11][OH:12])[O:7][C@@:6]1(S(C)(=O)=O)[N:13]1[CH:21]=[C:19]([CH3:20])[C:17](=[O:18])[NH:16][C:14]1=[O:15])(C)(=O)=O.[OH-].[Na+].[C@@H](N)(C(O)=O)[C@@H](F)C(N)=O.CC(C)([O-])C.[K+]>CS(C)=O.O>[CH3:20][C:19]1[C:17](=[O:18])[NH:16][C:14](=[O:15])[N:13]([C@@H:6]2[O:7][C@H:8]([CH2:11][OH:12])[CH:9]=[CH:5]2)[CH:21]=1

Participants

7

Reactant 4

HCID 14798Sodium HydroxideHCID 12635472016-54-7HCID 23665647Potassium tert-butoxideHCID 70036919HCID 70036919, compound

Product 1

HCID 18283StavudineYield 79%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Procedure

In this synthesis, dimesylthymidine 1 was first treated with sodium hydroxide (3 equivalents) in refluxing water for 2 hours and after work-up the resultant 3,5-anhydrothymidine was treated with potassium t-butoxide in dimethylsulfoxide (DMSO) at room temperature for 2 hours. The reaction mixture was neutralized, evaporated to dryness and after a series of manipulations which included extraction, decolourization, precipitation and recrystallization, gave Stavudine in 79% yield and an overall yield of 56%.

Workup

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

Sources & evidence

ORD record
ord-182aaade9989458b89f633f523d3aa88
Source dataset
uspto-grants-2003_10
Patent number
US06635753B1

Linked notes

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