Benzyl Chloride → HCID 58367486, compound
Reaction equation
[CH3:1][O:2][C:3]([C@@H:5]1[CH2:10][NH:9][CH2:8][CH2:7][N:6]1[C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])=[O:4].[CH2:18](Cl)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.C(N(CC)CC)C>C(#N)C>[CH3:1][O:2][C:3]([C@@H:5]1[CH2:10][N:9]([CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH2:8][CH2:7][N:6]1[C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])=[O:4]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 71 °C
Procedure
To a dry 100.0 ml one necked round bottom flask equipped with a stirring bar is added (S)-1-N-Boc-piperazine-2-carboxylic methyl ester (800 mg, 3.275 mmol) under N2. Anhydrous acetonitrile (20 ml) is added to the flask followed by benzyl chloride (0.38 ml, 3.275 mmol) and triethylamine (1.28 ml, 9.17 mmol). Condenser is then put on to the flask and the reaction mixture is heated at 71° C. for 20 minutes. The reaction mixture is allowed to come to room temperature and concentrated under reduced pressure. It is then diluted with dicholoromethane and washed with water and brine. The organic layer is dried over Na2SO4, filtered and concentrated under reduced pressure. The crude compound is flash column purified using hexane and ethylacetate gradient solvent system to yield 570 mg (52%) of the desired product.
Workup
- customCondenser is then put on to the flask
- customto come to room temperature
- concentrationconcentrated under reduced pressure
- additionIt is then diluted with dicholoromethane
- washwashed with water and brine
- dry with materialThe organic layer is dried over Na2SO4
- filtrationfiltered
- concentrationconcentrated under reduced pressure
- custompurified
Sources & evidence
- ORD record
- ord-24fa5f899c16441280329e2f68e43806
- Source dataset
- uspto-grants-2011_04
- Patent number
- US07932255B2
Reaction notes
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