(3-Bromopropyl)benzene → HCID 28567066, compound
Reaction equation
[CH3:1][O:2][C:3](=[O:6])[CH2:4][NH2:5].CCN(C(C)C)C(C)C.Br[CH2:17][CH2:18][CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.S([O-])([O-])(=O)=O.[Mg+2]>CN(C=O)C>[C:20]1([CH2:19][CH2:18][CH2:17][NH:5][CH2:4][C:3]([O:2][CH3:1])=[O:6])[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1Participants
6
Procedure
Under argon condition, glycine methyl ester (330 mg, 2.63 mmol) was dissolved in 3 mL of dry DMF and then DIPEA (573 μL, 3.29 mmol) and 1-bromo-3-phenylpropane (100 μL, 0.658 mmol) were added. The reaction mixture was then stirred for one day at room temperature. Upon completion of the reaction, the reaction was terminated by adding 5 mL of water, and the reaction mixture was extracted with diethyl ether (4 mL×4). The organic layer thus obtained was treated with anhydrous magnesium sulfate to remove water. The precipitate was filtered out and the resulting solution was concentrated by distillation under reduced pressure and purified by column chromatography to obtain 19.6 mg (0.0946 mmol, 14%) of the desired compound.
Workup
- customUpon completion of the reaction
- customthe reaction was terminated
- additionby adding 5 mL of water
- extractionthe reaction mixture was extracted with diethyl ether (4 mL×4)
- customThe organic layer thus obtained
- customto remove water
- filtrationThe precipitate was filtered out
- concentrationthe resulting solution was concentrated by distillation under reduced pressure
- custompurified by column chromatography
Sources & evidence
- ORD record
- ord-3f0839de10b14bb3941f2f218d601c8b
- Source dataset
- uspto-grants-2014_08
- Patent number
- US08809012B2
Reaction notes
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