4-Aminophenylacetic acid → 3-(4-Carboxymethyl-phenyl)-2-chloro-propionic acid 2,2,2-trichloro-ethyl ester

HRID 709450

Reaktionsgleichung

Reaktionsgleichung von HRID 709450
N[C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([OH:11])=[O:10])=[CH:4][CH:3]=1.[Cl:12][C:13]([Cl:21])([Cl:20])[CH2:14][O:15][C:16](=[O:19])[CH:17]=[CH2:18].COC(=O)C([Cl:35])CC1C=CC(CO)=CC=1>>[Cl:12][C:13]([Cl:21])([Cl:20])[CH2:14][O:15][C:16](=[O:19])[CH:17]([Cl:35])[CH2:18][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([OH:11])=[O:10])=[CH:4][CH:3]=1

Komponenten

4

Edukt 3

HCID 145334-Aminophenylacetic acidHCID 1817502,2,2-Trichloroethyl acrylateHCID 866502982-Chloro-3-(4-hydroxymethyl-phenyl)-propionic acid methyl ester

Produkt 1

HCID 866503013-(4-Carboxymethyl-phenyl)-2-chloro-propionic acid 2,2,2-trichloro-ethyl ester

Versuchsvorschrift

The title compound was prepared from 2-(4-amino phenyl)-acetic acid (1.00 g, 6.61 mmol) and acrylic acid 2,2,2-trichloroethyl ester (6.73 g, 33.08 mmol) as described for 2-chloro-3-(4-hydroxymethyl-phenyl)-propionic acid methyl ester. The crude product was purified by flash chromatography using DCM/MeOH 95:5 as the eluent to afford the product as an oil (1.17 g, 47.3%). 1H NMR (300 MHz, CDCl3): δ 7.17-7.33 (m, 4H), 4.73 (s, 2H), 4.52-4.56 (t, 1H), 3.60-3.63 (m, 2H), 3.37-3.42 (dd, 1H), 3.17-3.23 (dd, 1H).

Aufarbeitung

  1. customThe crude product was purified by flash chromatography

Quellen und Nachweise

ORD-Eintrag
ord-041afe5b309a4751abeaa995939fa4b7
Quelldatensatz
uspto-grants-2015_11
Patentnummer
US09181181B2

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