Benzyl chloroformate → HCID 13838839, compound

HRID 546465Notes

Reaction equation

HRID 546465 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[CH2:4][CH:5]=[CH:6][CH2:7][C@@H:2]1[NH:9][C:17]([O:19][CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)=[O:18])=[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. Water was poured into the reaction mixture to conduct extraction with methylene chloride, and the resultant organic layer was washed with saturated saline. The solvent was distilled off under reduced pressure, and the residue was purified by column chromatography on silica gel (dichloromethane) to obtain the title compound (8.22 g) as a colorless solid.

Workup

  1. additionwere added
  2. extractionextraction with methylene chloride
  3. washthe resultant organic layer was washed with saturated saline
  4. distillationThe solvent was distilled off under reduced pressure
  5. customthe residue was purified by column chromatography on silica gel (dichloromethane)

Sources & evidence

ORD record
ord-142fae5cc2554176ac308ac4f71752f0
Source dataset
uspto-grants-2011_05
Patent number
US07935824B2

Reaction notes

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