Water → (S)-tert-butyl(1-azidobutan-2-yl)carbamate

HRID 576694Notes

Reaction equation

HRID 576694 reaction equation
CS(O[CH2:6][C@@H:7]([NH:10][C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH2:8][CH3:9])(=O)=O.[N-:18]=[N+:19]=[N-:20].[Na+].O>CN(C=O)C>[C:14]([O:13][C:11](=[O:12])[NH:10][C@@H:7]([CH2:8][CH3:9])[CH2:6][N:18]=[N+:19]=[N-:20])([CH3:17])([CH3:16])[CH3:15]

Participants

5

Reactant 3

HCID 962WaterHCID 33557Sodium AzideHCID 89537961(S)-2-((tert-butoxycarbonyl)amino)butyl methanesulfonate

Product 1

HCID 131732866(S)-tert-butyl(1-azidobutan-2-yl)carbamate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
70 °C

Procedure

To a solution of (S)-2-((tert-butoxycarbonyl)amino)butyl methanesulfonate (13.4 g, 50 mmol) in DMF (100 mL) was added sodium azide (6.5 g, 100 mmol). The reaction mixture was heated at 70° C. for 18 h. After cooling to rt, water was added, and the reaction mixture was extracted with EtOAc. The combined organic extracts were washed with brine, dried (Na2SO4), filtered, and concentrated. Purification by chromatography (SiO2; 0-50% EtOAc/hexanes) provided the desired product as a white solid. 1H NMR (400 MHz, DMSO-d6) δ 6.87 (d, J=8.6 Hz, 1H), 3.54-3.37 (m, 1H), 3.27-3.20 (m, 2H), 1.45-1.25 (m, 2H), 1.39 (s, 9H), 0.82 (t, J=7.4 Hz, 3H).

Workup

  1. temperatureAfter cooling to rt
  2. extractionthe reaction mixture was extracted with EtOAc
  3. washThe combined organic extracts were washed with brine
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customPurification by chromatography (SiO2; 0-50% EtOAc/hexanes)

Sources & evidence

ORD record
ord-cd7981e43d374c73894516cd00d88114
Source dataset
uspto-grants-2015_05
Patent number
US09040534B2

Reaction notes

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