Sodium Azide → HCID 131732611, compound

HRID 878405Notes

Reaction equation

HRID 878405 reaction equation
CS(O[CH2:6][CH:7]([NH:12][C:13]([O:15][CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)=[O:14])[C:8]([F:11])([F:10])[F:9])(=O)=O.[N-:23]=[N+:24]=[N-:25].[Na+]>CN(C=O)C.O>[N:23]([CH2:6][CH:7]([NH:12][C:13](=[O:14])[O:15][CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[C:8]([F:11])([F:10])[F:9])=[N+:24]=[N-:25]

Participants

5

Reactant 2

HCID 33557Sodium AzideHCID 89486788Carbamic acid, N-[2,2,2-trifluoro-1-[[(methylsulfonyl)oxy]methyl]ethyl]-, phenylmethyl ester

Product 1

HCID 131732611HCID 131732611, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of 2-{[(benzyloxy)carbonyl]amino}-3,3,3-trifluoropropyl methanesulfonate (213 g, 625 mmol) in DMF (2500 mL) was added sodium azide (91.1 g, 1.40 mol). The reaction mixture was heated to 80° C. After 16 hours, the reaction mixture was diluted with water (1000 mL) and extracted with ethyl acetate (3×500 mL). The organics were combined, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was purified via chromatography on silica gel (10% ethyl acetate/petroleum ether) to afford benzyl (3-azido-1,1,1-trifluoropropan-2-yl)carbamate.

Workup

  1. extractionextracted with ethyl acetate (3×500 mL)
  2. dry with materialdried over anhydrous sodium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was purified via chromatography on silica gel (10% ethyl acetate/petroleum ether)

Sources & evidence

ORD record
ord-0a9423881be74a9e8c7f62e2e9866849
Source dataset
uspto-grants-2015_03
Patent number
US08987456B2

Reaction notes

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