Tetrabutylammonium Fluoride → 2-[3-Benzyloxy-4-(1,1,4-trioxo-1,2,5-thiadiazolidin-2-yl)-phenyl]-cyclopropanecarboxylic Acid Ethyl Ester

HRID 660644

Reaktionsgleichung

[CH2:1]([O:3][C:4]([CH:6]1[CH2:8][CH:7]1[C:9]1[CH:14]=[CH:13][C:12]([N:15]2[CH2:19][C:18](=[O:20])[N:17](CC[Si](C)(C)C)[S:16]2(=[O:28])=[O:27])=[C:11]([O:29][CH2:30][C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)[CH:10]=1)=[O:5])[CH3:2].CCCC[N+](CCCC)(CCCC)CCCC.[F-]>C1COCC1.CCOC(C)=O>[CH2:1]([O:3][C:4]([CH:6]1[CH2:8][CH:7]1[C:9]1[CH:14]=[CH:13][C:12]([N:15]2[CH2:19][C:18](=[O:20])[NH:17][S:16]2(=[O:27])=[O:28])=[C:11]([O:29][CH2:30][C:31]2[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=2)[CH:10]=1)=[O:5])[CH3:2]

Komponenten

Reaktionsbedingungen

Temperatur: 60 °C

Versuchsvorschrift

To 2-{3-benzyloxy-4-[1,1,4-trioxo-5-(2-trimethylsilanylethyl)-1,2,5-thiadiazolidin-2-yl]-phenyl}-cyclopropanecarboxylic acid ethyl ester (75 mg, 0.14 mmol) in THF (3 mL) is added 1M TBAF in THF (0.21 mL) and the solution is stirred at 60° C. for 2 h. The reaction is cooled to RT and diluted with EtOAc and washed with 1N HCl and brine. The organic layer is dried over MgSO4 and concentrated under reduced pressure to afford the title compound as a yellow oil, which is used in the next step without further purification: (M+H)+=448.

Aufarbeitung

temperatureThe reaction is cooled to RT
washwashed with 1N HCl and brine
dry with materialThe organic layer is dried over MgSO4
concentrationconcentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag: ord-45156971354f4dd3b0c217a724f12ccc
Quelldatensatz: uspto-grants-2011_12
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US08084448B2

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