Benzyl chloroformate → HCID 13838839, compound

HRID 2104363Notes

Reaction equation

HRID 2104363 reaction equation
Cl.[CH:2]1([NH2:9])[CH2:7][CH:6]=[CH:5][CH2:4][CH:3]1[NH2:8].Cl[C:11]([O:13][CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=[O:12].[C:21](=[O:24])([O-])[O-:22].[K+].[K+]>O.C(#N)C>[CH2:14]([O:22][C:21](=[O:24])[NH:8][C@H:3]1[C@@H:2]([NH:9][C:11]([O:13][CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[O:12])[CH2:7][CH:6]=[CH:5][CH2:4]1)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

6

Reactant 3

HCID 10387Benzyl chloroformateHCID 11430Potassium CarbonateHCID 19043994HCID 19043994, compound

Product 1

HCID 13838839HCID 13838839, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 6342AcetonitrileSolvent

Procedure

4-Cyclohexene-1,2-diamine hydrochloride (4.0 g) was dissolved in a solvent mixture of water (20 mL) and acetonitrile (20 mL), and to the solution were added benzyl chloroformate (7.66 mL) and potassium carbonate (14.9 g), followed by stirring at room temperature for 3 days. The reaction mixture was poured into water, and the thus-obtained mixture was extracted with methylene chloride. The organic layer was washed with saturated brine, and was dried over sodium sulfate anhydrate. The solvent was distilled away under reduced pressure, and the residue was purified by silica gel column chromatography (methylene chloride), to thereby give the title compound (8.22 g).

Workup

  1. extractionthe thus-obtained mixture was extracted with methylene chloride
  2. washThe organic layer was washed with saturated brine
  3. dry with materialwas dried over sodium sulfate anhydrate
  4. distillationThe solvent was distilled away under reduced pressure
  5. customthe residue was purified by silica gel column chromatography (methylene chloride)

Sources & evidence

ORD record
ord-687753b56f104e9b84c144b35c44d63f
Source dataset
uspto-grants-2009_08
Patent number
US07576135B2

Reaction notes

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