Sodium Azide → Carbamic acid, N-(2-azido-3,3,3-trifluoropropyl)-, phenylmethyl ester

HRID 1504806Notes

Reaction equation

HRID 1504806 reaction equation
FC(F)(F)S(O[CH:7]([CH2:12][NH:13][C:14]([O:16][CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)=[O:15])[C:8]([F:11])([F:10])[F:9])(=O)=O.[N-:26]=[N+:27]=[N-:28].[Na+]>CS(C)=O.O>[N:26]([CH:7]([C:8]([F:11])([F:10])[F:9])[CH2:12][NH:13][C:14](=[O:15])[O:16][CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)=[N+:27]=[N-:28]

Participants

5

Reactant 2

HCID 33557Sodium AzideHCID 86731687HCID 86731687, compound

Product 1

HCID 86731688Carbamic acid, N-(2-azido-3,3,3-trifluoropropyl)-, phenylmethyl ester

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Conditions

Temperature
40 °C

Procedure

To a solution of 3-{[(benzyloxy)carbonyl]amino}-1,1,1-trifluoropropan-2-yl trifluoromethanesulfonate (150 g, 380 mmol) in DMSO (1200 mL) was added sodium azide (36.5 g, 562 mmol). The reaction mixture was heated to 40° C. After 5 hours, the reaction mixture was diluted with water (1000 mL) and extracted with diethyl ether (3×1200 mL). The organic layers were combined, dried over anhydrous sodium sulfate, filtered, and concentrated under reduced pressure to afford benzyl (2-azido-3,3,3-trifluoropropyl)carbamate. The material was used without further purification.

Workup

  1. extractionextracted with diethyl ether (3×1200 mL)
  2. dry with materialdried over anhydrous sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-c208952b9a93413891690a1da5a4edda
Source dataset
uspto-grants-2015_12
Patent number
US09216173B2

Reaction notes

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