Citric Acid → 3-[N-(t-butoxycarbonyl)-N-(2-cyclohexylethyl)amino]propionic acid
Reaction equation
Cl.[CH:2]1([CH2:8][CH2:9][NH:10][CH2:11][CH2:12][C:13]([OH:15])=[O:14])[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3]1.[C:16](=O)([O:22]C(C)(C)C)[O:17][C:18]([CH3:21])([CH3:20])[CH3:19].C(N(CC)CC)C.C(O)(=O)CC(CC(O)=O)(C(O)=O)O>O1CCCC1>[C:18]([O:17][C:16]([N:10]([CH2:11][CH2:12][C:13]([OH:15])=[O:14])[CH2:9][CH2:8][CH:2]1[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3]1)=[O:22])([CH3:21])([CH3:20])[CH3:19]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Procedure
Next, tetrahydrofuran (8 ml) was added to 3-[N-(2-cyclohexylethyl)amino]propionic acid hydrochloride (1.0 g, 4.2 mmol), and the mixture was stirred at room temperature. Di-t-butyl carbonate (1.1 g, 5.1 mmol) and triethylamine (1.3 ml, 9.3 mmol) were added to the mixture, the whole was stirred overnight, and then a 5% aqueous citric acid solution (10 ml) was added to the reaction mixture. The whole was extracted with chloroform (60 ml), and the organic layer was washed with saturated brine (20 ml). The organic layer was dried over magnesium sulfate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography to give 0.79 g (62%) of 3-[N-(t-Butoxycarbonyl)-N-(2-cyclohexylethyl)amino]propionic acid as a colorless oily matter.
Workup
- stirringthe whole was stirred overnight
- extractionThe whole was extracted with chloroform (60 ml)
- washthe organic layer was washed with saturated brine (20 ml)
- dry with materialThe organic layer was dried over magnesium sulfate
- concentrationconcentrated under reduced pressure
- customThe residue was purified by silica gel column chromatography
Sources & evidence
- ORD record
- ord-162ae1bc4d2c46db837e10599d56dfa9
- Source dataset
- uspto-grants-2008_03
- Patent number
- US07345064B2
Reaction notes
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