Water → HCID 86635695, compound

HRID 598867Notes

Reaction equation

HRID 598867 reaction equation
CS(O[CH2:6][CH2:7][C@@H:8]([NH:20][C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[CH2:9][C:10]1[CH:15]=[CH:14][C:13]([C:16]([F:19])([F:18])[F:17])=[CH:12][CH:11]=1)(=O)=O.[N-:28]=[N+:29]=[N-:30].[Na+].O.CCOC(C)=O>CN(C=O)C>[N:28]([CH2:6][CH2:7][C@@H:8]([NH:20][C:21](=[O:22])[O:23][C:24]([CH3:27])([CH3:26])[CH3:25])[CH2:9][C:10]1[CH:15]=[CH:14][C:13]([C:16]([F:19])([F:18])[F:17])=[CH:12][CH:11]=1)=[N+:29]=[N-:30]

Participants

6

Reactant 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 33557Sodium AzideHCID 86635694HCID 86635694, compound

Product 1

HCID 86635695HCID 86635695, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
70 °C

Procedure

(S)-3-(tert-Butoxycarbonylamino)-4-(4-(trifluoromethyl)phenyl)butyl methanesulfonate from the previous reaction was dissolved in 25 mL DMF and NaN3 (1.3 g, 20 mmol) was added. The mixture was heated to 70° C. for 4 hours and cooled back to room temperature. Water and EtOAc were added and the phases were separated. The aqueous phase was extracted with EtOAc (3×100 mL) and the combined organic layers were dried over MgSO4 and evaporated. Glass column chromatography (10% EtOAc in hexanes) provided the title compound as white solid. LCMS (API-ES) m/z (%): 259.0 (100%, M++H).

Workup

  1. temperaturecooled back to room temperature
  2. customthe phases were separated
  3. extractionThe aqueous phase was extracted with EtOAc (3×100 mL)
  4. dry with materialthe combined organic layers were dried over MgSO4
  5. customevaporated

Sources & evidence

ORD record
ord-9038d007d9034a3a80eeef61188692b6
Source dataset
uspto-grants-2011_03
Patent number
US07897619B2

Reaction notes

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