(3R)-3-(3-(((2-(5,5-Dimethyl-1-cyclopenten-1-yl)-2'-fluoro-5'-(methyloxy)-1,1'-biphenyl-4-yl)methyl)oxy)phenyl)-4-(methyloxy)butanoic acid → 1-(3-(Benzyloxy)phenyl)-2-methoxyethanone
Reaktionsgleichung
CC1(C)C([C:7]2[CH:12]=[C:11]([CH2:13][O:14][C:15]3[CH:16]=[C:17]([C@H:21]([CH2:26][O:27][CH3:28])CC(O)=O)[CH:18]=[CH:19][CH:20]=3)[CH:10]=[CH:9][C:8]=2C2C=C(OC)C=CC=2F)=CCC1.CC1(C)C(C2C=C(C[O:52]C3C=C([C@@H](COC)CC(O)=O)C=CC=3)C=CC=2C2C=C(OC)C=CC=2F)=CCC1>>[CH2:13]([O:14][C:15]1[CH:16]=[C:17]([C:21](=[O:52])[CH2:26][O:27][CH3:28])[CH:18]=[CH:19][CH:20]=1)[C:11]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:12]=1Komponenten
3
Edukt 2
HCID 57706590(3R)-3-(3-(((2-(5,5-Dimethyl-1-cyclopenten-1-yl)-2'-fluoro-5'-(methyloxy)-1,1'-biphenyl-4-yl)methyl)oxy)phenyl)-4-(methyloxy)butanoic acid
HCID 57707078(3S)-3-(3-(((2-(5,5-dimethyl-1-cyclopenten-1-yl)-2'-fluoro-5'-(methyloxy)-1,1'-biphenyl-4-yl)methyl)oxy)phenyl)-4-(methyloxy)butanoic acidProdukt 1
Versuchsvorschrift
(3R)-3-(3-(((2-(5,5-Dimethyl-1-cyclopenten-1-yl)-2′-fluoro-5′-(methyloxy)-1,1′-biphenyl-4-yl)methyl)oxy)phenyl)-4-(methyloxy)butanoic acid or (3S)-3-(3-(((2-(5,5-dimethyl-1-cyclopenten-1-yl)-2′-fluoro-5′-(methyloxy)-1,1′-biphenyl-4-yl)methyl)oxy)phenyl)-4-(methyloxy)butanoic acid (74). Compound 74.2 was obtained from compound 74.1 by a method analogous to that used for the preparation of compound 5.7 as described in Example 5 using a Peterson olefination followed by hydrogenation and final chiral separation. Coupling with 14.5 and hydrolysis was carried out according to the methods described herein. 1H NMR (400 MHz, CDCl3) δ ppm 7.39 (dd, 1H), 7.33 (d, 1H), 7.28 (d, 1H), 7.24 (t, 1H), 6.96 (t, 1H), 6.88 (m, 2H), 6.84 (bd, 1H), 6.79 (m, 2H), 5.52 (bt, 1H), 5.08 (s, 2H), 3.75 (s, 3H), 3.56 (dd, 1H), 3.48 (t, 1H), 3.40 (m, 1H), 3.33 (s, 3H), 2.88 (dd, 1H), 2.65 (dd, 1H), 2.24 (dt, 2H), 1.65 (t, 2H), 0.85 (s, 6H).