HCID 59094529, compound → HCID 59094532, compound

HRID 1168292Notes

Reaction equation

HRID 1168292 reaction equation
[CH3:1][O:2][C@H:3]1[C@@H:7]2[O:8][C:9]([CH3:12])([CH3:11])[O:10][C@@H:6]2[C@@H:5]([C:13]([NH:15][NH:16][C:17](=[S:26])[NH:18][CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)=O)[O:4]1>[OH-].[Na+]>[CH3:1][O:2][C@H:3]1[C@@H:7]2[O:8][C:9]([CH3:12])([CH3:11])[O:10][C@@H:6]2[C@@H:5]([C:13]2[N:18]([CH2:19][C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[C:17](=[S:26])[NH:16][N:15]=2)[O:4]1

Participants

3

Reactant 1

HCID 59094529HCID 59094529, compound

Product 1

HCID 59094532HCID 59094532, compoundYield 39.1%

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Procedure

A solution of 2-{[(3aS,4S,6R,6aR)-6-methoxy-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl]carbonyl}-N-benzylhydrazinecarbothioamide (Preparation 17) (5.9 g, 15.5 mmol) in 2 M aqueous sodium hydroxide (200 ml) was heated under reflux for 2 hours. The solution was allowed to cool to room temperature and extracted with dichloromethane (50 ml). The aqueous phase was then acidified to pH 4 with 2 M aqueous hydrochloric acid and extracted with ethyl acetate (300 ml). The ethyl acetate layer was dried (anhydrous magnesium sulphate) and evaporated under reduced pressure to give the title compound (2.20 g).

Workup

  1. temperatureunder reflux for 2 hours
  2. extractionextracted with dichloromethane (50 ml)
  3. extractionextracted with ethyl acetate (300 ml)
  4. dry with materialThe ethyl acetate layer was dried (anhydrous magnesium sulphate)
  5. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-da4facf3085e4d9fbef17d073b6cb6a9
Source dataset
uspto-grants-2003_09
Patent number
US06624158B2

Reaction notes

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