Water → HCID 15287332, compound

HRID 627581Notes

Reaction equation

HRID 627581 reaction equation
CS(O[CH2:6][CH2:7][CH2:8][NH:9][C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])(=O)=O.[N-:17]=[N+:18]=[N-:19].[Na+].O>CN(C=O)C>[C:13]([O:12][C:10](=[O:11])[NH:9][CH2:8][CH2:7][CH2:6][N:17]=[N+:18]=[N-:19])([CH3:16])([CH3:15])[CH3:14]

Participants

5

Reactant 3

HCID 962WaterHCID 33557Sodium AzideHCID 114141093-((Tert-butoxycarbonyl)amino)propyl methanesulfonate

Product 1

HCID 15287332HCID 15287332, compoundYield 87.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of compound 5 (12.56 g: 60 mmol) in dry DMF (150 mL) was added in small portions NaN3 (11.7 g: 180 mmol) with stirring over 30 min. The resulting solution was heated to 50° C. for 1 h and then stirred overnight at room temperature. Water (50 mL) was added with stirring, the solvent was removed, and the residue was extracted with ethyl acetate (2×175 mL). The combined organic layers were washed sequentially with water (2×50 mL) and brine (2×50 mL). The organic extract was dried over anhydrous sodium sulfate and evaporated to give compound 6 as a light yellow oil (10.54 g; 87% yield). 1H NMR (CDCl3-d6) δ 4.9 (s, 1H), 3.3 (m, 2H), 3.2 (m, 2H), 1.7 (m, 2H), 1.4 (s, 9H).

Workup

  1. stirringstirred overnight at room temperature
  2. stirringwith stirring
  3. customthe solvent was removed
  4. extractionthe residue was extracted with ethyl acetate (2×175 mL)
  5. washThe combined organic layers were washed sequentially with water (2×50 mL) and brine (2×50 mL)
  6. extractionThe organic extract
  7. dry with materialwas dried over anhydrous sodium sulfate
  8. customevaporated

Sources & evidence

ORD record
ord-0d342b47d08d4100bed903dbd3c1872b
Source dataset
uspto-grants-2016_04
Patent number
US09309284B2

Reaction notes

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