1-Bromooctane → HCID 43088882, 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][CH2:20][CH2:21][CH2:22][CH2:23][CH3:24].S([O-])([O-])(=O)=O.[Mg+2]>CN(C=O)C>[CH2:17]([NH:5][CH2:4][C:3]([O:2][CH3:1])=[O:6])[CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH3:24]Participants
6
Procedure
Under argon condition, glycine methyl ester (358 mg, 2.85 mmol) was dissolved in 2 mL of dry DMF, and then DIPEA (620 μL, 3.56 mmol) and 1-bromooctane (123 μL, 0.712 mmol) were added, and the reaction mixture was 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 31.6 mg (0.157 mmol, 22%) 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-ce77b99aa85d4220877abbb2d06404b2
- Source dataset
- uspto-grants-2014_08
- Patent number
- US08809012B2
Reaction notes
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