Water → HCID 86678007, compound

HRID 246709Notes

Reaction equation

HRID 246709 reaction equation
CS(O[CH2:6][C:7]1([NH:10][C:11]([O:13][CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[O:12])[CH2:9][CH2:8]1)(=O)=O.[N-:21]=[N+:22]=[N-:23].[Na+].O>CN(C=O)C>[N:21]([CH2:6][C:7]1([NH:10][C:11](=[O:12])[O:13][CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH2:9][CH2:8]1)=[N+:22]=[N-:23]

Participants

5

Reactant 3

HCID 962WaterHCID 33557Sodium AzideHCID 58049436HCID 58049436, compound

Product 1

HCID 86678007HCID 86678007, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
70 °C

Procedure

To a stirred solution of (1-(benzyloxycarbonylamino)cyclopropyl)methyl methanesulfonate (5 g, 16.7 mmol) in 100 mL of DMF was added NaN3 (3 g, 46.15 mmol) in one portion at room temperature. Then the reaction mixture was stirred at 70° C. for 16 hours. The mixture was poured into 400 mL of water, extracted with ethyl acetate (600 mL). The organic phase was washed with brine (50 mL) and dried over anhydrous sodium sulfate. The drying agent was removed by filtration and the filtrate was evaporated at 40° C. under reduced pressure to give a crude product as colorless oil, which was used in the next step without further purification MS: (M+H)+=247.2.

Workup

  1. extractionextracted with ethyl acetate (600 mL)
  2. washThe organic phase was washed with brine (50 mL)
  3. dry with materialdried over anhydrous sodium sulfate
  4. customThe drying agent was removed by filtration
  5. customthe filtrate was evaporated at 40° C. under reduced pressure

Sources & evidence

ORD record
ord-20c109456dbf4a2aa027c7ff3ac060b9
Source dataset
uspto-grants-2014_02
Patent number
US08658646B2

Reaction notes

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