Sodium Azide → 1-[(2S,4R)-4-azido-5-methoxy-tetrahydrofuran-2-yl]ethyl benzoate

HRID 60726Notes

Reaction equation

HRID 60726 reaction equation
[C:1]([O:9][CH:10]([C@@H:12]1[CH2:16][C@H:15](OS(C(F)(F)F)(=O)=O)[CH:14]([O:25][CH3:26])[O:13]1)[CH3:11])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[N-:27]=[N+:28]=[N-:29].[Na+]>CN(C=O)C>[C:1]([O:9][CH:10]([C@@H:12]1[CH2:16][C@@H:15]([N:27]=[N+:28]=[N-:29])[CH:14]([O:25][CH3:26])[O:13]1)[CH3:11])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 33557Sodium AzideHCID 1213963371-[(2S,4S)-5-methoxy-4-(trifluoromethylsulfonyloxy)tetrahydrofuran-2-yl]ethyl benzoate2×

Product 1

HCID 1213963101-[(2S,4R)-4-azido-5-methoxy-tetrahydrofuran-2-yl]ethyl benzoateYield 206%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 1-[(2S,4S)-5-methoxy-4-(trifluoromethylsulfonyloxy)tetrahydrofuran-2-yl]ethyl benzoate (compound 25j, 400 mg, 1 mmol) in DMF (2 mL) was added sodium azide (65 mg, 1.05 mmol) at room temperature and the mixture was stirred at room temperature for 16 hours. The reaction mixture was partitioned between EtOAc and H2O, the organic layer was separated and the aqueous layer was extracted with EtOAc twice. The organic layers were combined, washed with brine, dried over Na2SO4 and concentrated in vacuo to afford 600 mg crude product of 1-[(2S,4R)-4-azido-5-methoxy-tetrahydrofuran-2-yl]ethyl benzoate (compound 25k), which was used in next step without further purification.

Workup

  1. customThe reaction mixture was partitioned between EtOAc and H2O
  2. customthe organic layer was separated
  3. extractionthe aqueous layer was extracted with EtOAc twice
  4. washwashed with brine
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-b1a861c84d1d49639445c0ed10b7978f
Source dataset
uspto-grants-2016_09
Patent number
US09441008B2

Reaction notes

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