Ethanol → HCID 22175261, Verbindung

Reaktionsgleichung

[CH:1]1[C:13]2[CH:12]([CH2:14][O:15][C:16](=[O:42])[NH:17][CH2:18][C:19]3[N:20]([CH2:38][CH:39]([CH3:41])[CH3:40])[C:21](=[O:37])[C:22]4[C:27]([C:28]=3[O:29][CH2:30][CH2:31][CH2:32][CH3:33])=[CH:26][C:25]([C:34]([NH2:36])=[S:35])=[CH:24][CH:23]=4)[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]=2[CH:4]=[CH:3][CH:2]=1.Cl[CH2:44][C:45]([O:47][CH2:48][CH3:49])=[O:46].O.[CH2:51](O)[CH3:52]>>[CH2:30]([O:29][C:28]1[C:27]2[C:22](=[CH:23][CH:24]=[C:25]([C:34]3[S:35][C:44]([C:45]([O:47][CH2:48][CH3:49])=[O:46])=[C:51]([CH3:52])[N:36]=3)[CH:26]=2)[C:21](=[O:37])[N:20]([CH2:38][CH:39]([CH3:41])[CH3:40])[C:19]=1[CH2:18][NH:17][C:16]([O:15][CH2:14][CH:12]1[C:11]2[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=2[C:5]2[C:13]1=[CH:1][CH:2]=[CH:3][CH:4]=2)=[O:42])[CH2:31][CH2:32][CH3:33]

Komponenten

Edukt 4

HCID 702Ethanol

HCID 962Water

HCID 7751Ethyl chloroacetate

HCID 22176325HCID 22176325, Verbindung

Produkt 1

HCID 22175261HCID 22175261, VerbindungAusbeute 65,3 %

Versuchsvorschrift

A solution of 9H-fluoren-9-ylmethyl[6-(aminocarbothioyl)-4-butoxy-2-isobutyl-1-oxo-1,2-dihydro-3-isoquinolinyl]methylcarbamate (2.33 g, 4 mmol) and ethyl 2-chloroacetate (1.32 g, 8 mmol) in ethanol (20 ml) was refluxed under heating for 10 h. The resulting reaction mixture was poured into water and extracted with ethyl acetate. The extract was washed with brine, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography to give ethyl 2-[4-butoxy-3-({[(9H-fluoren-9-ylmethoxy)carbonyl]amino}methyl)-2-isobutyl-1-oxo-1,2-dihydro-6-isoquinolinyl]-4methyl-1,3-thiazole-5-carboxylate (1.81 g, 65.3%) as crystals.