Water → HCID 60207723, compound

HRID 1776144Notes

Reaction equation

HRID 1776144 reaction equation
CS(O[CH2:6][CH2:7]/[CH:8]=[CH:9]/[CH2:10][C:11]([NH:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[NH:20][C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])=[O:12])(=O)=O.[NH3:28].O.O>CN(C=O)C>[NH2:28][CH2:6][CH2:7]/[CH:8]=[CH:9]/[CH2:10][C:11]([NH:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[NH:20][C:21](=[O:22])[O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:12]

Participants

5

Reactant 3

HCID 962WaterHCID 12896473Azane;hydrateHCID 60207708(E)-6-(2-(tert-butoxycarbonylamino)phenylamino)-6-oxohex-3-enyl methanesulfonate

Product 1

HCID 60207723HCID 60207723, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of (E)-6-(2-(tert-butoxycarbonylamino)phenylamino)-6-oxohex-3-enyl methanesulfonate (358 mg, 0.9 mmol) in DMF (5 mL) was added NH3.H2O (20 mL) at 0° C. and stirred at the same temperature for 0.5 hour, then the reaction mixture was stirred at room temperature for 12 hr, then water (100 mL) was added, the mixture was extracted with DCM (3×50 mL), the combined organic layers were washed with brine, dried over Na2SO4 and concentrated to give the desired compound of (E)-tert-butyl 2-(6-aminohex-3-enamido)phenylcarbamate (100 mg, 88%) as a white solid after purification by column chromatography (eluent: DCM:MeOH=50:1).

Workup

  1. stirringthe reaction mixture was stirred at room temperature for 12 hr
  2. extractionthe mixture was extracted with DCM (3×50 mL)
  3. washthe combined organic layers were washed with brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-306f9e4f9e34438fadb47b59b203c74d
Source dataset
uspto-grants-2016_02
Patent number
US09265734B2

Reaction notes

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