Hydrochloric Acid → HCID 178499978, compound
Reaction equation
Cl.C(OC([NH:9][CH2:10][CH2:11][O:12][C:13]1[CH:43]=[CH:42][C:16]([CH2:17]/[C:18](=[C:23](\[C@H:28]2[CH2:33][CH2:32][C@@H:31]([O:34][Si](C(C)(C)C)(C)C)[CH2:30][CH2:29]2)/[C:24]([O:26][CH3:27])=[O:25])/[C:19]([O:21][CH3:22])=[O:20])=[CH:15][CH:14]=1)=O)(C)(C)C>C(O)C>[NH2:9][CH2:10][CH2:11][O:12][C:13]1[CH:14]=[CH:15][C:16]([CH2:17]/[C:18](=[C:23](\[C@H:28]2[CH2:33][CH2:32][C@@H:31]([OH:34])[CH2:30][CH2:29]2)/[C:24]([O:26][CH3:27])=[O:25])/[C:19]([O:21][CH3:22])=[O:20])=[CH:42][CH:43]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 50 °C
Procedure
Concentrated hydrochloric acid (catalytic amount) was added to a solution of dimethyl 2-(4-(2-((tert-butoxycarbonyl)amino)ethoxy)benzyl)-3-(cis-4-((tert-butyldimethylsilyl)oxy)cyclohexyl)maleate (20 mg, 0.033 mmol) in ethanol (1.0 ml) at room temperature, and the mixture was stirred at 50° C. for 15 hr. This mixture was concentrated, and sodium bicarbonate water was added to the residue, followed by extraction with dichloromethane. The organic layer was washed with water and saturated brine and was dried over anhydrous magnesium sulfate, and the filtrate was concentrated. The residue was chromatographed on silica gel column (methanol:dichloromethane=1:9) to give the title compound as an oil (10 mg, yield 83%).
Workup
- concentrationThis mixture was concentrated
- additionsodium bicarbonate water was added to the residue
- extractionfollowed by extraction with dichloromethane
- washThe organic layer was washed with water and saturated brine
- dry with materialwas dried over anhydrous magnesium sulfate
- concentrationthe filtrate was concentrated
- customThe residue was chromatographed on silica gel column (methanol:dichloromethane=1:9)
Sources & evidence
- ORD record
- ord-27036281172841348b03124aff58cc62
- Source dataset
- uspto-grants-2015_08
- Patent number
- US09115079B2
Reaction notes
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