Sodium Azide → HCID 178454124, compound

HRID 707265Notes

Reaction equation

HRID 707265 reaction equation
CS(O[C@H:6]1[CH2:9][C@@H:8]([NH:10][C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH2:7]1)(=O)=O.[N-:18]=[N+:19]=[N-:20].[Na+]>CN(C=O)C.O>[C:14]([O:13][C:11](=[O:12])[NH:10][C@H:8]1[CH2:9][C@@H:6]([N:18]=[N+:19]=[N-:20])[CH2:7]1)([CH3:17])([CH3:16])[CH3:15]

Participants

5

Reactant 2

HCID 33557Sodium AzideHCID 178454135HCID 178454135, compound

Product 1

HCID 178454124HCID 178454124, compoundYield 95.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
85 °C

Procedure

To a solution of cis-3-((tert-butoxycarbonyl)amino)cyclobutyl methanesulfonate (29 g, 109 mmol) in DMF (100 mL) was added sodium azide (5.68 mL, 162 mmol) portionwise and the mixture stirred at 85° C. for 18 h. After cooling, the reaction mixture was diluted with water (200 mL) and extracted with EtOAc (3×100 mL). The combined organic was washed with water (2×100 mL) and brine, dried over Na2SO4 and evaporated in vacuo to give the desired product tert-butyl(cis-3-azidocyclobutyl)carbamate (22 g, 104 mmol, 95% yield) that was used in the next step without further purification. 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 4.68 (br. s., 1 H), 3.87 (br. s., 1 H), 3.44-3.68 (m, 1 H), 2.75 (d, J=6.85 Hz, 2 H), 1.90 (q, J=9.19 Hz, 2 H), 1.44 (s, 10 H).

Workup

  1. temperatureAfter cooling
  2. extractionextracted with EtOAc (3×100 mL)
  3. washThe combined organic was washed with water (2×100 mL) and brine
  4. dry with materialdried over Na2SO4
  5. customevaporated in vacuo

Sources & evidence

ORD record
ord-73171e2e4752401dacf57695c19f168a
Source dataset
uspto-grants-2015_11
Patent number
US09174992B2

Reaction notes

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