(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

HRID 1662501Notes

Reaction equation

HRID 1662501 reaction equation
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]=1

Participants

3

Reactant 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 acidHCID 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 acid

Product 1

HCID 197934711-(3-(Benzyloxy)phenyl)-2-methoxyethanone

Procedure

(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).

Sources & evidence

ORD record
ord-1711fee0cf7543ed9ae7c9cac7e43f25
Source dataset
uspto-grants-2011_10
Patent number
US08030354B2

Reaction notes

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