Lithium hydroxide, monohydrate → 1-(2-Oxo-2,3-dihydro-1,3-benzoxazol-5-YL)cyclopropane-1-carboxylic acid

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Reaktionsgleichung

C[O:2][C:3]([C:5]1([C:8]2[CH:9]=[CH:10][C:11]3[O:15][C:14](=[O:16])[NH:13][C:12]=3[CH:17]=2)[CH2:7][CH2:6]1)=[O:4].O[Li].O>CO.O>[O:16]=[C:14]1[NH:13][C:12]2[CH:17]=[C:8]([C:5]3([C:3]([OH:4])=[O:2])[CH2:7][CH2:6]3)[CH:9]=[CH:10][C:11]=2[O:15]1

Komponenten

Reaktionsbedingungen

Temperatur: 50 °C

Versuchsvorschrift

To a solution of 1-(2-oxo-2,3-dihydro-benzooxazol-5-yl)-cyclopropanecarboxylic acid methyl ester (1.9 g, 8.1 mmol) in MeOH (20 mL) and water (2 mL) was added LiOH.H2O (1.7 g, 41 mmol) in portions at room temperature. The reaction mixture was stirred for 20 hours at 50° C. MeOH was removed by evaporation under vacuum before water (100 mL) and EtOAc (50 mL) were added. The aqueous layer was separated, acidified with HCl (3 mol/L) and extracted with EtOAc (100 mL×3). The combined organic layers were dried over anhydrous Na2SO4 and evaporated under vacuum to give 1-(2-oxo-2,3-dihydrobenzo[d]oxazol-5-yl)cyclopropanecarboxylic acid (1.5 g, 84%). 1H NMR (DMSO, 400 MHz) δ 12.32 (brs, 1H), 11.59 (brs, 1H), 7.16 (d, J=8.4 Hz, 1H), 7.00 (d, J=8.0 Hz, 1H), 1.44-1.41 (m, 2H), 1.13-1.10 (m, 2H). MS (ESI) m/e (M+H+) 218.1.

Aufarbeitung

customMeOH was removed by evaporation under vacuum before water (100 mL) and EtOAc (50 mL)
additionwere added
customThe aqueous layer was separated
extractionextracted with EtOAc (100 mL×3)
dry with materialThe combined organic layers were dried over anhydrous Na2SO4
customevaporated under vacuum

Quellen und Nachweise

ORD-Eintrag: ord-2a84f0b3e1804d209deb6909dd4fc867
Quelldatensatz: uspto-grants-2014_12
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US08912199B2

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