Acetic Acid → [3-(4-Chlorophenylsulfanyl)-4-(hydroxyimino)-2-methyl-4,5,6,7-tetrahydro-1H-indol-1-yl]acetic acid
Reaktionsgleichung
[OH-].[Na+].O.[Cl:4][C:5]1[CH:10]=[CH:9][C:8]([S:11][C:12]2[C:20]3[C:19](=[N:21][OH:22])[CH2:18][CH2:17][CH2:16][C:15]=3[N:14]([CH2:23][C:24]([O:26]CC)=[O:25])[C:13]=2[CH3:29])=[CH:7][CH:6]=1.C(O)(=O)C>C(O)C>[Cl:4][C:5]1[CH:10]=[CH:9][C:8]([S:11][C:12]2[C:20]3[C:19](=[N:21][OH:22])[CH2:18][CH2:17][CH2:16][C:15]=3[N:14]([CH2:23][C:24]([OH:26])=[O:25])[C:13]=2[CH3:29])=[CH:7][CH:6]=1Komponenten
6
Reaktionsbedingungen
- Temperatur
- 40 °C
Versuchsvorschrift
Aqueous sodium hydroxide (1M, 10 mL, 10 mmol) and water (20 mL) were added to a stirred suspension of ethyl [3-(4-chloro-phenylsulfanyl)-4-(hydroxyimino)-2-methyl-4,5,6,7-tetrahydro-1H-indol-1-yl]acetate (4.0 g, 10.2 mmol) and ethanol 40 mL) and the mixture was warmed up to 40° C. After 1.5 h at this temperature, the reaction mixture was allowed to cool to r.t. and held overnight. The suspension was reheated to 33° C. and acetic acid (1.7 mL, 29.7 mmol) added to the resulting solution. The mixture was allowed to cool to r.t., the solid product was collected by filtration, washed with water (2×20 mL), then dried under vacuum at 30° C. to provide the title compound as a solid; 2.94 g (79%); purity by HPLC 98.9 area %
Aufarbeitung
- temperatureto cool to r.t.
- waitheld overnight
- customwas reheated to 33° C.
- temperatureto cool to r.t.
- filtrationthe solid product was collected by filtration
- washwashed with water (2×20 mL)
- customdried under vacuum at 30° C.
Quellen und Nachweise
- ORD-Eintrag
- ord-9306a98cc8954d31868dc64429fe6f64
- Quelldatensatz
- uspto-grants-2012_07
- Patentnummer
- US08227622B2
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