Benzyl chloroformate → HCID 13838839, compound

HRID 902846Notes

Reaction equation

HRID 902846 reaction equation
Cl.[CH:2]1([NH2:9])[CH2:7][CH:6]=[CH:5][CH2:4][CH:3]1[NH2:8].[C:10](=[O:13])([O-:12])[O-].[K+].[K+].Cl[C:17]([O:19][CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)=[O:18]>O.C(#N)C>[CH2:20]([O:12][C:10]([NH:8][C@@H:3]1[C@H:2]([NH:9][C:17](=[O:18])[O:19][CH2:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[CH2:7][CH:6]=[CH:5][CH2:4]1)=[O:13])[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=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 mixed solvent of water (20 ml) and acetonitrile (20 ml), and benzyl chloroformate (7.66 ml) and potassium carbonate (14.9 g) were added, and the mixture was stirred at room temperature for 3 days. The reaction mixture was poured into water to conduct extraction with methylene chloride. The resultant organic layer was washed with saturated aqueous solution of sodium chloride, and dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure, and the residue was purified by column chromatography on silica gel (methylene chloride) to obtain the title compound (8.22 g).

Workup

  1. additionwere added
  2. extractionextraction with methylene chloride
  3. washThe resultant organic layer was washed with saturated aqueous solution of sodium chloride
  4. dry with materialdried over anhydrous sodium sulfate
  5. distillationThe solvent was distilled off under reduced pressure
  6. customthe residue was purified by column chromatography on silica gel (methylene chloride)

Sources & evidence

ORD record
ord-21652ce31cd64ffd8a4e4df1f45bd454
Source dataset
uspto-grants-2008_04
Patent number
US07365205B2

Reaction notes

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