Water → Tert-butyl {5-[2-(benzyloxy)ethoxy]pyrazin-2-yl}carbamate
Reaction equation
[CH2:1]([O:8][CH2:9][CH2:10][O:11][C:12]1[N:13]=[CH:14][C:15](C(O)=O)=[N:16][CH:17]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([N:23]([CH2:26]C)CC)C.C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:35])C=CC=CC=1.O.[C:46]([OH:50])([CH3:49])([CH3:48])[CH3:47]>>[CH2:1]([O:8][CH2:9][CH2:10][O:11][C:12]1[N:13]=[CH:14][C:15]([NH:23][C:26](=[O:35])[O:50][C:46]([CH3:49])([CH3:48])[CH3:47])=[N:16][CH:17]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1Participants
Procedure
5-[2-(Benzyloxy)ethoxy]pyrazine-2-carboxylic acid (1.089 g) was suspended in tert-butyl alcohol (20 mL), and triethylamine (0.66 mL) and diphenylphosphoryl azide (0.9 mL) were added thereto. The reaction mixture was heated under reflux overnight and left to be cooled to room temperature. To the reaction mixture was added water, followed by extraction with ethyl acetate. The organic layer was sequentially washed with saturated aqueous sodium bicarbonate and saturated brine, and then dried over anhydrous magnesium sulfate. It was concentrated under reduced pressure, and the obtained crude product was purified by silica gel column chromatography (hexane:ethyl acetate=5:1-3:1) to obtain tert-butyl {5-[2-(benzyloxy)ethoxy]pyrazin-2-yl}carbamate (1.352 g) as a white solid.
Workup
- temperatureThe reaction mixture was heated
- temperatureunder reflux overnight
- waitleft
- extractionfollowed by extraction with ethyl acetate
- washThe organic layer was sequentially washed with saturated aqueous sodium bicarbonate and saturated brine
- dry with materialdried over anhydrous magnesium sulfate
- concentrationIt was concentrated under reduced pressure
- customthe obtained crude product
- customwas purified by silica gel column chromatography (hexane:ethyl acetate=5:1-3:1)
Sources & evidence
- ORD record
- ord-c220927ab80846d9856ac095201107d3
- Source dataset
- uspto-grants-2012_12
- Patent number
- US08329707B2
Reaction notes
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