Diisopropylethylamine → Rac-{[6-chloro-3-(3-chloro-benzyl)-2-oxo-2,3-dihydro-1h-indol-3-yl]-isopropyl-amino}-acetic acid ethyl ester

HRID 556487

Reaktionsgleichung

Reaktionsgleichung von HRID 556487
Br[C:2]1([CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([Cl:20])[CH:15]=2)[C:10]2[C:5](=[CH:6][C:7]([Cl:11])=[CH:8][CH:9]=2)[NH:4][C:3]1=[O:12].[CH2:21]([O:23][C:24](=[O:30])[CH2:25][NH:26][CH:27]([CH3:29])[CH3:28])[CH3:22].CCN(C(C)C)C(C)C>ClCCl>[CH2:21]([O:23][C:24](=[O:30])[CH2:25][N:26]([C:2]1([CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([Cl:20])[CH:15]=2)[C:10]2[C:5](=[CH:6][C:7]([Cl:11])=[CH:8][CH:9]=2)[NH:4][C:3]1=[O:12])[CH:27]([CH3:29])[CH3:28])[CH3:22]

Komponenten

5

Edukt 3

HCID 81531DiisopropylethylamineHCID 351625Ethyl 2-((propan-2-yl)amino)acetateHCID 575072733-Bromo-6-chloro-3-(3-chloro-benzyl)-1,3-dihydro-indol-2-one

Produkt 1

HCID 57479121Rac-{[6-chloro-3-(3-chloro-benzyl)-2-oxo-2,3-dihydro-1h-indol-3-yl]-isopropyl-amino}-acetic acid ethyl esterAusbeute 87,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

At room temperature, 3-Bromo-6-chloro-3-(3-chloro-benzyl)-1,3-dihydro-indol-2-one (4.57 g, 12.3 mmol) and Isopropylamino-acetic acid ethyl ester (2.15 g, 14.8 mmol), DIPEA (2.14 ml) were mixed in about 40 ml dichloromethane. After stirred for about 3 h, the solution was concentrated and the crude product was purified by chromatography to obtain 4.7 g solid rac-{[6-Chloro-3-(3-chloro-benzyl)-2-oxo-2,3-dihydro-1H-indol-3-yl]-isopropyl-amino}-acetic acid ethyl ester. MS: 435 (M+H)+.

Aufarbeitung

  1. concentrationthe solution was concentrated
  2. customthe crude product was purified by chromatography

Quellen und Nachweise

ORD-Eintrag
ord-1525746dbb864f61938c59cf6c78caf3
Quelldatensatz
uspto-grants-2011_11
Patentnummer
US08058269B2

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