Water → 3-(4-Tert-butylphenylsulfonamido)thieno[2,3-b]pyridine-2-carboxylic acid

HRID 1925728Notizen

Reaktionsgleichung

[C:1]([C:5]1[CH:10]=[CH:9][C:8]([S:11]([NH:14][C:15]2[C:23]3[C:18](=[N:19][CH:20]=[CH:21][CH:22]=3)[S:17][C:16]=2[C:24]([O:26]C)=[O:25])(=[O:13])=[O:12])=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].[OH-].[Na+].O>O1CCCC1>[C:1]([C:5]1[CH:10]=[CH:9][C:8]([S:11]([NH:14][C:15]2[C:23]3[C:18](=[N:19][CH:20]=[CH:21][CH:22]=3)[S:17][C:16]=2[C:24]([OH:26])=[O:25])(=[O:12])=[O:13])=[CH:7][CH:6]=1)([CH3:4])([CH3:2])[CH3:3]

Komponenten

Reaktionsbedingungen

Temperatur: 50 °C

Versuchsvorschrift

To a solution of 94 (0.070 g; 0.17 mmol) in tetrahydrofuran (2 mL), aqueous sodium hydroxide (2 mL; 4 mmol; 2N) and water (4 mL) were added. The reaction mixture was heated at 50° C. for 5 hours, cooled to room temperature, and then extracted with diethyl ether (2×). The ether solution was discarded. The aqueous layer was acidified with aqueous hydrochloric acid (2N) and extracted with ethyl acetate. The organic layer was separated and washed with aqueous saturated sodium chloride, dried over magnesium sulfate filtered, and evaporated under reduced pressure to yield the title compound as an off-white solid (0.067 g).

Aufarbeitung

temperaturecooled to room temperature
extractionextracted with diethyl ether (2×)
extractionextracted with ethyl acetate
customThe organic layer was separated
washwashed with aqueous saturated sodium chloride
dry with materialdried over magnesium sulfate
filtrationfiltered
customevaporated under reduced pressure

Quellen und Nachweise

ORD-Eintrag: ord-835f1beef9c04b598d579f8a5cef6595
Quelldatensatz: uspto-grants-2012_05
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US08178699B2

Notizen zur Reaktion

Wird geladen…