Hydrochloric Acid → (R)-methyl 2-(quinolin-8-yloxy)propanoate

HRID 1507017Notes

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]=1

Participants

Conditions

Temperature: 25 °C

Procedure

To a solution 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), DEAD (430 mg, 2.47 mmol) and the resulting mixture was stirred at 25° C. for 16 h. Aqueous HCl (1M, 10 mL) was added, the mixture separated, and the aqueous layer extracted with ethyl acetate. The aqueous portion was basified by addition of saturated aqueous NaHCO3 (20 mL) and extracted with ethyl acetate. The combined organic extracts were washed with brine, dried over sodium sulfate and concentrated. The residue was purified by column chromatography. (300 mg, yield 63%) MS (ESI+) e/z: 232.1 [M+1]+.

Workup

customthe mixture separated
extractionthe aqueous layer extracted with ethyl acetate
additionThe aqueous portion was basified by addition of saturated aqueous NaHCO3 (20 mL)
extractionextracted with ethyl acetate
washThe combined organic extracts were washed with brine
dry with materialdried over sodium sulfate
concentrationconcentrated
customThe residue was purified by column chromatography

Sources & evidence

ORD record: ord-91e88ff0112a43afbea818480f958f46
Source dataset: uspto-grants-2015_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09221794B2

Reaction notes

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