2-Fluoro-4'-hydroxybenzophenone → (2S)-3-(4-{3-[4-(2-Fluoro-benzoyl)-phenoxy]-propoxy}-phenyl)-2-methoxy-propionic acid
Reaktionsgleichung
[OH:1][CH2:2][CH2:3][CH2:4][O:5][C:6]1[CH:11]=[CH:10][C:9]([CH2:12][C@H:13]([O:17][CH3:18])[C:14]([OH:16])=[O:15])=[CH:8][CH:7]=1.[F:19][C:20]1[CH:34]=[CH:33][CH:32]=[CH:31][C:21]=1[C:22]([C:24]1[CH:29]=[CH:28][C:27](O)=[CH:26][CH:25]=1)=[O:23]>>[F:19][C:20]1[CH:34]=[CH:33][CH:32]=[CH:31][C:21]=1[C:22]([C:24]1[CH:29]=[CH:28][C:27]([O:1][CH2:2][CH2:3][CH2:4][O:5][C:6]2[CH:11]=[CH:10][C:9]([CH2:12][C@H:13]([O:17][CH3:18])[C:14]([OH:16])=[O:15])=[CH:8][CH:7]=2)=[CH:26][CH:25]=1)=[O:23]Komponenten
3
Versuchsvorschrift
The title compound was prepared from (2S)-3-[4-(3-Hydroxy-propoxy)-phenyl]-2-methoxy-propionic acid linked to Wang's Resin (Example 94, Step D) via Mitsunobu coupling with 2-fluoro-4′-hydroxybenzophenone and cleavage from the resin (Standard Procedure G) gave an oily solid (7%). 1H-NMR (200.15 MHz, CDCl3): δ 7.81 (dd, 2H, J=8.8, 1.3), 7.54–7.45 (m, 2H), 7.28–7.09 (m, 4H), 6.94 (d, 2H, J=8.6), 6.83 (d, 2H, J=8.6), 4.24 (t, 2H, J=6.2), 4.14 (t, 2H, J=6.2), 3.98 (dd, 1H, J=7.0, 4.6), 3.40 (s, 3H), 3.09 (dd, 1H, J=14.2, 4.6), 2.96 (dd, 1H, J=14.2, 7.0), 2.28 (q, 2H, J=6.2).
Quellen und Nachweise
- ORD-Eintrag
- ord-dcd20a4377d143abbac3ac5c89c0c7e0
- Quelldatensatz
- uspto-grants-2007_03
- Patentnummer
- US07192982B2
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