2-Chlorophenol → 3-{3-[3-(2-Chloro-phenoxy)-propoxy]-phenyl}-2-methoxy-propionic acid

HRID 459361Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 459361
C[O:2][C:3](=[O:19])[CH:4]([O:17][CH3:18])[CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([O:12][CH2:13][CH2:14][CH2:15]Br)[CH:7]=1.[Cl:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=1[OH:27].CO[C@@H](CC1C=CC(OCCCOC2C=CC=CC=2)=CC=1)C(O)=O>>[Cl:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=1[O:27][CH2:15][CH2:14][CH2:13][O:12][C:8]1[CH:7]=[C:6]([CH2:5][CH:4]([O:17][CH3:18])[C:3]([OH:2])=[O:19])[CH:11]=[CH:10][CH:9]=1

Komponenten

4

Edukt 3

HCID 72452-ChlorophenolHCID 588228613-[3-(3-Bromo-propoxy)-phenyl]-2-methoxy-propionic acid methyl esterHCID 58822897(2S)-2-methoxy-3-[4-(3-phenoxy propoxy)-phenyl]-propionic acid

Produkt 1

HCID 184435923-{3-[3-(2-Chloro-phenoxy)-propoxy]-phenyl}-2-methoxy-propionic acid

Versuchsvorschrift

The title compound was prepared from 3-[3-(3-bromo-propoxy)-phenyl]-2-methoxy-propionic acid methyl ester (Example 323, Step 1) and 2-chlorophenol via the same procedure used for the preparation of (2S)-2-methoxy-3-[4-(3-phenoxy-propoxy)-phenyl]-propionic acid (Example 285, Step 1). The enatiomers were separated by chiral HPLC. 1H-NMR (CDCl3, 200.15 MHz): 7.35 (dd, 1H, J=8.1, 1.9), 7.24–7.16 (m, 2H), 6.97–6.80 (m, 5H), 4.22 (t, 2H, J=5.9), 4.20 (t, 2H, J=5.9), 4.02 (dd, 1H, J=7.3, 4.0), 3.39 (s, 3H), 3.13 (dd, 1H, J=14.2, 3.8), 2.97 (dd, 1H, J=14.0, 7.8), 2.30 (qn, 2H, J=6.2).

Aufarbeitung

  1. customThe enatiomers were separated by chiral HPLC

Quellen und Nachweise

ORD-Eintrag
ord-13d31f6af5884acb8a5b46ab652d7479
Quelldatensatz
uspto-grants-2007_03
Patentnummer
US07192982B2

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