Sodium Azide → HCID 86731694, compound

HRID 1504809Notes

Reaction equation

HRID 1504809 reaction equation
FC(F)(F)S(O[CH:7]([CH2:11][NH:12][C:13]([O:15][CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)=[O:14])[CH:8]([F:10])[F:9])(=O)=O.[N-:25]=[N+:26]=[N-:27].[Na+]>CN(C=O)C.O>[N:25]([CH:7]([CH:8]([F:10])[F:9])[CH2:11][NH:12][C:13](=[O:14])[O:15][CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)=[N+:26]=[N-:27]

Participants

5

Reactant 2

HCID 33557Sodium AzideHCID 86731693HCID 86731693, compound

Product 1

HCID 86731694HCID 86731694, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of 3-{[(benzyloxy)carbonyl]amino}-1,1-difluoropropan-2-yl trifluoromethanesulfonate (580 g, 1.54 mol) in DMF (3000 mL) was added sodium azide (240 g, 3.69 mol). After 3 hours, the reaction mixture was diluted with water (3000 mL) and extracted with diethyl ether (3×1500 mL). The organic layers were combined, dried over anhydrous sodium sulfate, filtered, and concentrated under reduced pressure to afford benzyl (2-azido-3,3-difluoropropyl)carbamate. The material was used without further purification.

Workup

  1. extractionextracted with diethyl ether (3×1500 mL)
  2. dry with materialdried over anhydrous sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-c5e03b60965c414f816cbf494f893991
Source dataset
uspto-grants-2015_12
Patent number
US09216173B2

Reaction notes

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