Potassium Carbonate → Ethyl 3-phenyl-3-[6-(tert-butoxycarbonylmethoxy)indol-3-yl]propionate

HRID 351930

Reaktionsgleichung

Reaktionsgleichung von HRID 351930
[C:1]1([CH:7]([C:14]2[C:22]3[C:17](=[CH:18][C:19]([OH:23])=[CH:20][CH:21]=3)[NH:16][CH:15]=2)[CH2:8][C:9]([O:11][CH2:12][CH3:13])=[O:10])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Br[CH2:25][C:26]([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:27].C(=O)([O-])[O-].[K+].[K+].C1(C)C=CC=CC=1.CC(C)=O>CC(C)=O>[C:1]1([CH:7]([C:14]2[C:22]3[C:17](=[CH:18][C:19]([O:23][CH2:25][C:26]([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:27])=[CH:20][CH:21]=3)[NH:16][CH:15]=2)[CH2:8][C:9]([O:11][CH2:12][CH3:13])=[O:10])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Komponenten

6

Edukt 4

HCID 11430Potassium CarbonateHCID 79177tert-Butyl bromoacetateHCID 15549281Ethyl 3-phenyl-3-(6-hydroxyindol-3-yl)propionateHCID 20247278Toluene acetone

Produkt 1

HCID 22714448Ethyl 3-phenyl-3-[6-(tert-butoxycarbonylmethoxy)indol-3-yl]propionate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 180AcetoneLösungsmittel

Versuchsvorschrift

The compound ethyl 3-phenyl-3-(6-hydroxyindol-3-yl)propionate 4 prepared analogously to Example 1.1-1.3 (3.23 mmol) is stirred overnight at 60° C. with 0.94 ml (6.4 mmol) of tert-butyl bromoacetate and 1.8 g (13 mmol) of potassium carbonate in 20 ml of acetone. When the reaction is complete (TLC check toluene/acetone 4:1), the residue is filtered off, the solution is evaporated, and the crude product is purified by chromatography on silica gel (eluent toluene/acetone 9:1), giving ethyl 3-phenyl-3-[6-(tert-butoxycarbonylmethoxy)indol-3-yl]propionate.

Aufarbeitung

  1. filtrationthe residue is filtered off
  2. customthe solution is evaporated
  3. customthe crude product is purified by chromatography on silica gel (eluent toluene/acetone 9:1)

Quellen und Nachweise

ORD-Eintrag
ord-aedfb14ae3144d6d8767b8e89bac1c8d
Quelldatensatz
uspto-grants-2004_06
Patentnummer
US06743810B2

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