Diethyl Ether → HCID 86612127, compound
Reaction equation
CO[C:3](=[O:15])[C@H:4]([CH2:13][OH:14])[NH:5][C:6]([O:8][C:9]([CH3:12])([CH3:11])[CH3:10])=[O:7].[CH2:16]([Mg]Br)[CH3:17].[Cl-].[NH4+].[CH2:22](OCC)[CH3:23]>>[CH2:22]([C:3]([OH:15])([CH2:16][CH3:17])[CH:4]([NH:5][C:6](=[O:7])[O:8][C:9]([CH3:10])([CH3:11])[CH3:12])[CH2:13][OH:14])[CH3:23]Participants
Conditions
- Temperature
- -78 °C
Procedure
Boc-serine methyl ester (6.30 g) was dissolved in diethyl ether (150 ml), and a solution of ethyl magnesium bromide (in 3 M diethyl ether, 57 ml) was added dropwise thereto while the mixture was cooled to −78° C. After addition by dropping, the temperature of the reaction mixture was elevated to room temperature, and mixed at room temperature for 2 hours. The reaction mixture was again cooled to 0° C., and a saturated aqueous ammonium chloride solution was added dropwise thereto. The organic layer was collected by separation, and the aqueous layer was extracted three times with ethyl acetate. The extracts were all mixed, washed with saturated brine and dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure to obtain the title compound as a colorless oil (1.10 g, 79%).
Workup
- additionAfter addition
- customwas elevated to room temperature
- additionmixed at room temperature for 2 hours
- temperatureThe reaction mixture was again cooled to 0° C.
- customThe organic layer was collected by separation
- extractionthe aqueous layer was extracted three times with ethyl acetate
- washwashed with saturated brine
- dry with materialdried over anhydrous sodium sulfate
- distillationThe solvent was distilled off under reduced pressure
Sources & evidence
- ORD record
- ord-c72482ae0e904dc294830f218d6dc719
- Source dataset
- uspto-grants-2010_10
- Patent number
- US07820673B2
Reaction notes
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