Sodium Azide → HCID 86731705, compound

HRID 1504825Notes

Reaction equation

HRID 1504825 reaction equation
CS(O[CH2:6][CH:7]([NH:12][C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[CH2:8][O:9][CH2:10][CH3:11])(=O)=O.[N-:20]=[N+:21]=[N-:22].[Na+]>CN(C=O)C.O>[N:20]([CH2:6][CH:7]([NH:12][C:13](=[O:14])[O:15][C:16]([CH3:19])([CH3:18])[CH3:17])[CH2:8][O:9][CH2:10][CH3:11])=[N+:21]=[N-:22]

Participants

5

Reactant 2

HCID 33557Sodium AzideHCID 86731704HCID 86731704, compound

Product 1

HCID 86731705HCID 86731705, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of 2-[(tert-butoxycarbonyl)amino]-3-ethoxypropyl methanesulfonate (1.6 g, 5.4 mmol) in DMF (20 mL) was added sodium azide (1.10 g, 16.2 mmol) and then the reaction mixture was heated to 50° C. After 24 hours, the reaction mixture was diluted with water and the aqueous layer was extracted with ethyl acetate. The combined organic layers were concentrated under reduced pressure and the resulting residue was purified via silica chromatography to give tert-butyl (1-azido-3-ethoxypropan-2-yl)carbamate. MS ESI calc'd. for C10H21N4O3 [M+H]+ 245. found 245.

Workup

  1. extractionthe aqueous layer was extracted with ethyl acetate
  2. concentrationThe combined organic layers were concentrated under reduced pressure
  3. customthe resulting residue was purified via silica chromatography

Sources & evidence

ORD record
ord-e886e654ca934a63b37826638c081999
Source dataset
uspto-grants-2015_12
Patent number
US09216173B2

Reaction notes

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