2-(4-Fluorophenyl)ethane-1-thiol → 2-[2-(4-Fluoro-phenyl)-ethylsulfanyl]-3-(4-(2-hydroxy-ethyl)-phenyl)-propionic acid 2,2,2-trichloro-ethyl ester

HRID 1628141Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1628141
[Cl:1][C:2]([Cl:20])([Cl:19])[CH2:3][O:4][C:5](=[O:18])[CH:6](Cl)[CH2:7][C:8]1[CH:13]=[CH:12][C:11]([CH2:14][CH2:15][OH:16])=[CH:10][CH:9]=1.[F:21][C:22]1[CH:27]=[CH:26][C:25]([CH2:28][CH2:29][SH:30])=[CH:24][CH:23]=1.COC(=O)C(SCCC1C=CC(F)=CC=1)CC1C=CC(C(C)(C)O[SiH2]C(C)(C)C)=CC=1>>[Cl:1][C:2]([Cl:20])([Cl:19])[CH2:3][O:4][C:5](=[O:18])[CH:6]([S:30][CH2:29][CH2:28][C:25]1[CH:26]=[CH:27][C:22]([F:21])=[CH:23][CH:24]=1)[CH2:7][C:8]1[CH:13]=[CH:12][C:11]([CH2:14][CH2:15][OH:16])=[CH:10][CH:9]=1

Komponenten

4

Edukt 3

HCID 186687292-(4-Fluorophenyl)ethane-1-thiolHCID 866502992-Chloro-3-[4-(2-hydroxy-ethyl)-phenyl]-propionic acid 2,2,2-trichloro-ethyl esterHCID 1317316773-[4-(Tert-butyl-dimethyl-silanyloxy-methyl)-phenyl]-2-[2-(4-fluoro-phenyl)-ethylsulfanyl]-propionic acid methyl ester

Produkt 1

HCID 668651452-[2-(4-Fluoro-phenyl)-ethylsulfanyl]-3-(4-(2-hydroxy-ethyl)-phenyl)-propionic acid 2,2,2-trichloro-ethyl ester

Versuchsvorschrift

The title compound was prepared from 2-chloro-3-[4-(2-hydroxy-ethyl)-phenyl]-propionic acid 2,2,2-trichloro-ethyl ester (2.57 g, 7.14 mmol) and 2-(4-fluoro-phenyl)-ethanethiol (1.23 g, 7.85 mmol) as described for 3-[4-(tert-butyl-dimethyl-silanyloxy-methyl)-phenyl]-2-[2-(4-fluoro-phenyl)-ethylsulfanyl]-propionic acid methyl ester. After purification by flash chromatography with n-heptane/EtOAc 5:1 as the eluent the product was obtained as an oil (1.0 g, 29.2%). 1H NMR (300 MHz, CDCl3): δ 7.10-7.14 (m, 6H), 6.93-6.99 (t, 2H), 4.65-4.76 (q, 2H), 3.82-3.86 (t, 2H), 3.55-3.60 (dd, 2H), 3.17-3.25 (dd, 2H), 2.81-3.00 (m, 7H).

Aufarbeitung

  1. customAfter purification by flash chromatography with n-heptane/EtOAc 5:1 as the eluent the product

Quellen und Nachweise

ORD-Eintrag
ord-a11b587834214227a53bd1f71dfe83a1
Quelldatensatz
uspto-grants-2014_07
Patentnummer
US08785681B2

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