Methyl 3-(3-hydroxyphenyl)propionate → 3-(3-(((2-(Butyloxy)-2'-fluoro-5'-(methyloxy)-1,1'-biphenyl-4-yl)methyl)oxy)phenyl)propanoic acid

HRID 1662333Notes

Reaction equation

HRID 1662333 reaction equation
OC1C=C(CCC(OC)=O)C=CC=1.[CH2:14]([O:18][C:19]1[CH:24]=[C:23]([CH2:25][O:26][C:27]2[CH:28]=[C:29]([C@@H:33](C(F)(F)F)[CH2:34][C:35]([OH:37])=[O:36])[CH:30]=[CH:31][CH:32]=2)[CH:22]=[CH:21][C:20]=1[C:42]1[CH:47]=[C:46]([O:48][CH3:49])[CH:45]=[CH:44][C:43]=1[F:50])[CH2:15][CH2:16][CH3:17]>>[CH2:14]([O:18][C:19]1[CH:24]=[C:23]([CH2:25][O:26][C:27]2[CH:28]=[C:29]([CH2:33][CH2:34][C:35]([OH:37])=[O:36])[CH:30]=[CH:31][CH:32]=2)[CH:22]=[CH:21][C:20]=1[C:42]1[CH:47]=[C:46]([O:48][CH3:49])[CH:45]=[CH:44][C:43]=1[F:50])[CH2:15][CH2:16][CH3:17]

Participants

3

Reactant 2

HCID 1512675Methyl 3-(3-hydroxyphenyl)propionateHCID 25261468(3S)-3-(3-(((2-(butyloxy)-2'-fluoro-5'-(methyloxy)-1,1'-biphenyl-4-yl)methyl)oxy)phenyl)-4,4,4-trifluorobutanoic acid

Product 1

HCID 577065513-(3-(((2-(Butyloxy)-2'-fluoro-5'-(methyloxy)-1,1'-biphenyl-4-yl)methyl)oxy)phenyl)propanoic acid

Procedure

Compound 13 was synthesized from methyl 3-(3-hydroxyphenyl)propanoate (available from Aagile Labs Division of Tyger Scientific) and 5.4 by a method analogous to the method used to prepare compound 7. ESI (neg.) m/e: 451.1 (M−H)+. 1H NMR (400 MHz, CDCl3) δ ppm 7.22-7.32 (2H, m), 7.01-7.09 (3H, m), 6.82-6.91 (5H, m), 5.08 (2H, s), 4.00 (2H, t, J=6.5 Hz), 3.81 (3H, s), 2.97 (2H, t, J=7.8 Hz), 2.71 (2H, t, J=7.8 Hz), 1.64-1.72 (2H, m), 1.34-1.43 (2H, m), 0.90 (3H, t, J=7.3 Hz).

Sources & evidence

ORD record
ord-0b387a2637234844ba7ff65702cb5e92
Source dataset
uspto-grants-2011_10
Patent number
US08030354B2

Reaction notes

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