Sodium Hydroxide → 4-(2-Methyl-thiazol-4-ylmethoxy)-1H-indole-2-carboxylic acid
Reaktionsgleichung
CC[O:3][C:4]([C:6]1[N:7](C(OC(C)(C)C)=O)[C:8]2[C:13]([CH:14]=1)=[C:12]([O:15][CH2:16][C:17]1[N:18]=[C:19]([CH3:22])[S:20][CH:21]=1)[CH:11]=[CH:10][CH:9]=2)=[O:5].[OH-].[Na+]>C(O)C>[CH3:22][C:19]1[S:20][CH:21]=[C:17]([CH2:16][O:15][C:12]2[CH:11]=[CH:10][CH:9]=[C:8]3[C:13]=2[CH:14]=[C:6]([C:4]([OH:5])=[O:3])[NH:7]3)[N:18]=1Komponenten
4
Reaktionsbedingungen
- Temperatur
- 60 °C
Versuchsvorschrift
4-(2-Methyl-thiazol-4-ylmethoxy)-indole-1,2-dicarboxylic acid 1-tert-butyl ester 2-ethyl ester (169) (1.75 g, 4.2 mmol) is dissolved in 20 ml of ethanol. After addition of a 0.5M aqueous sodium hydroxide solution (33.6 ml, 16.8 mmol) the solution is heated to 60° C. and stirred at this temperature for 18 h. Then the reaction mixture is evaporated and the residue is dissolved in ethyl acetate. AT 0° C. conc HCl is added until a pH of 1 is reached. The organic phase is washed with water and brine. The organic layers are dried over sodium sulphate, filtrated. The product crystallized upon evaporation and could be filtrated off.
Aufarbeitung
- customThen the reaction mixture is evaporated
- dissolutionthe residue is dissolved in ethyl acetate
- additionAT 0° C. conc HCl is added until a pH of 1
- washThe organic phase is washed with water and brine
- dry with materialThe organic layers are dried over sodium sulphate
- filtrationfiltrated
- customThe product crystallized upon evaporation
- filtrationcould be filtrated off
Quellen und Nachweise
- ORD-Eintrag
- ord-912c649fffd144dab955a9b9c1f4812d
- Quelldatensatz
- uspto-grants-2010_12
- Patentnummer
- US07858781B2
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