Hydrochloric Acid → (R)-methyl 2-(quinolin-8-yloxy)propanoate
Reaction equation
[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][C:9]=2[OH:11])[CH:4]=[CH:3][CH:2]=1.O[C@@H:13]([CH3:18])[C:14]([O:16][CH3:17])=[O:15].C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.CCOC(/N=N/C(OCC)=O)=O.Cl>C1COCC1>[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][C:9]=2[O:11][C@H:13]([CH3:18])[C:14]([O:16][CH3:17])=[O:15])[CH:4]=[CH:3][CH:2]=1Participants
7
Conditions
- Temperature
- 25 °C
Procedure
To a stirred mixture of quinolin-8-ol (300 mg, 2.07 mmol) in THF (5 mL) was added (S)-methyl 2-hydroxypropanoate (215 mg, 2.07 mmol), PPh3 (647 mg, 2.47 mmol) and DEAD (430 mg, 2.47 mmol). The mixture was stirred at 25° C. for 16 hours. Subsequently, 1M HCl was added (10 mL) and the solution was washed with EtOAc (20 mL×3). The pH of the aqueous solution was raised by addition of aqueous NaHCO3 (10 mL), and then this solution was washed with EtOAc (10 mL×3). The combined organic extracts were washed with brine (20 mL), dried over anhydrous Na2SO4 and concentrated. The residue was purified by silica column chromatography to afford the product as a colorless oil (300 mg, 62.5% yield). LCMS (m/z): 233.1 [M+H]+
Workup
- washthe solution was washed with EtOAc (20 mL×3)
- temperatureThe pH of the aqueous solution was raised by addition of aqueous NaHCO3 (10 mL)
- washthis solution was washed with EtOAc (10 mL×3)
- washThe combined organic extracts were washed with brine (20 mL)
- dry with materialdried over anhydrous Na2SO4
- concentrationconcentrated
- customThe residue was purified by silica column chromatography
Sources & evidence
- ORD record
- ord-dc7f0f36f25c4ba48ddd3550370545fb
- Source dataset
- uspto-grants-2015_01
- Patent number
- US08940726B2
Reaction notes
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