Tetrahydrofuran → N-[2-(1,3-Thiazol-2-yl)-1H-indol-7-yl]-N-(2-thienylsulfonyl)aminoacetic acid

HRID 1851531Notizen

Reaktionsgleichung

[S:1]1[CH:5]=[CH:4][N:3]=[C:2]1[C:6]1[NH:7][C:8]2[C:13]([CH:14]=1)=[CH:12][CH:11]=[CH:10][C:9]=2[N:15]([CH2:24][C:25]([O:27]CC)=[O:26])[S:16]([C:19]1[S:20][CH:21]=[CH:22][CH:23]=1)(=[O:18])=[O:17].[OH-].[Na+].O1CCCC1>CO>[S:1]1[CH:5]=[CH:4][N:3]=[C:2]1[C:6]1[NH:7][C:8]2[C:13]([CH:14]=1)=[CH:12][CH:11]=[CH:10][C:9]=2[N:15]([CH2:24][C:25]([OH:27])=[O:26])[S:16]([C:19]1[S:20][CH:21]=[CH:22][CH:23]=1)(=[O:18])=[O:17]

Komponenten

Reaktionsbedingungen

Temperatur: 60 °C

Versuchsvorschrift

A mixture of ethyl N-[2-(1,3-thiazol-2-yl)-1H-indol-7-yl]-N-(2-thienylsulfonyl)aminoacetate (0.29 g), 1N aqueous sodium hydroxide solution (2.0 mL), tetrahydrofuran (5 mL) and methanol (5 mL) was stirred at 60° C. for 1 hr. The reaction mixture was concentrated, and water was added to the residue. The mixture was acidified with 10% aqueous citric acid solution, and the resulting crystals were filtrated, washed with water and dried. The obtained crystals were dissolved in tetrahydrofuran, treated with activated carbon, and concentrated to give the title compound (0.19 g, yield 69%) as colorless crystals. melting point>218° C. (decomposition).

Aufarbeitung

concentrationThe reaction mixture was concentrated
additionwater was added to the residue
filtrationthe resulting crystals were filtrated
washwashed with water
customdried
dissolutionThe obtained crystals were dissolved in tetrahydrofuran
additiontreated with activated carbon
concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag: ord-2d1892b4c28e4ee3b6445d0a582bbf10
Quelldatensatz: uspto-grants-2015_02
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US08957070B2

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