Sodium Azide → [(2S,4R,5R)-4-azido-5-methoxy-tetrahydrofuran-2-yl]methyl benzoate

HRID 60752Notes

Reaction equation

HRID 60752 reaction equation
[C:1]([O:9][CH2:10][C@@H:11]1[CH2:15][C@H:14](OS(C(F)(F)F)(=O)=O)[CH:13]([O:24][CH3:25])[O:12]1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[N-:26]=[N+:27]=[N-:28].[Na+]>CN(C=O)C.O>[C:1]([O:9][CH2:10][C@@H:11]1[CH2:15][C@@H:14]([N:26]=[N+:27]=[N-:28])[C@H:13]([O:24][CH3:25])[O:12]1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 33557Sodium AzideHCID 121396343[(2S,4S)-5-methoxy-4-(trifluoromethylsulfonyloxy)tetrahydrofuran-2-yl]methyl benzoate2×

Product 1

HCID 121396352[(2S,4R,5R)-4-azido-5-methoxy-tetrahydrofuran-2-yl]methyl benzoateYield 141.7%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of [(2S,4S)-5-methoxy-4-(trifluoromethylsulfonyloxy)tetrahydrofuran-2-yl]methyl benzoate (compound 32c, 1.1 g, 2.8 mmol) in DMF (5 mL) was added sodium azide (372 mg, 5.7 mmol) at room temperature and the mixture was stirred at room temperature for 16 hours. The reaction mixture was diluted with water and extracted with EtOAc, the organic layers were combined and concentrated in vacuo to afford 1.1 g crude product of [(2S,4R,5R)-4-azido-5-methoxy-tetrahydrofuran-2-yl]methyl benzoate (compound 33a) as an oil, which was used in next step without further purification.

Workup

  1. extractionextracted with EtOAc
  2. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-d01fd081414b401386e019450581d53b
Source dataset
uspto-grants-2016_09
Patent number
US09441008B2

Reaction notes

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