Potassium Bromide → 3-{4-[2-(2-Cyclohexyl-5-methyl-oxazol-4-yl)-ethoxy]-phenyl}-2-methyl-2-(4-trifluoromethyl-phenoxy)-propionic Acid

HRID 585230Notes

Reaction equation

HRID 585230 reaction equation
C([O:3][C:4](=[O:26])[C:5]([CH3:25])([O:14][C:15]1[CH:20]=[CH:19][C:18]([C:21]([F:24])([F:23])[F:22])=[CH:17][CH:16]=1)[CH2:6][C:7]1[CH:12]=[CH:11][C:10]([OH:13])=[CH:9][CH:8]=1)C.[CH:27]1([C:33]2[O:34][C:35]([CH3:51])=[C:36]([CH2:38][CH2:39]OS(C3C=CC(C)=CC=3)(=O)=O)[N:37]=2)[CH2:32][CH2:31][CH2:30][CH2:29][CH2:28]1.[K+].[Br-]>>[CH:27]1([C:33]2[O:34][C:35]([CH3:51])=[C:36]([CH2:38][CH2:39][O:13][C:10]3[CH:11]=[CH:12][C:7]([CH2:6][C:5]([CH3:25])([O:14][C:15]4[CH:20]=[CH:19][C:18]([C:21]([F:22])([F:23])[F:24])=[CH:17][CH:16]=4)[C:4]([OH:3])=[O:26])=[CH:8][CH:9]=3)[N:37]=2)[CH2:28][CH2:29][CH2:30][CH2:31][CH2:32]1

Participants

4

Reactant 3

HCID 253877Potassium BromideHCID 22340021Toluene-4-sulfonic acid 2-(2-cyclohexyl-5-methyloxazol-4-yl)-ethyl esterHCID 693173822-(4-Trifluoromethylphenoxy)-3-(4-hydroxyphenyl)-2-methyl-propionic acid ethyl ester

Product 1

HCID 223399753-{4-[2-(2-Cyclohexyl-5-methyl-oxazol-4-yl)-ethoxy]-phenyl}-2-methyl-2-(4-trifluoromethyl-phenoxy)-propionic Acid

Procedure

The title compound was prepared from 3-(4-hydroxyphenyl)-2-methyl-2-(4-trifluoromethyl-phenoxy)propionic acid ethyl ester and toluene-4-sulfonic acid 2-(2-cyclohexyl-5-methyl-oxazol-4-yl)-ethyl ester using the procedure of Example 50. 1H NMR (400 MHz, CDCl3) δ 7.48 (d, 2H, J=8.8 Hz), 7.16 (d, 2H, J=8.8 Hz), 6.95 (d, 2H, J=8.4 Hz), 6.78 (d, 2H, J=8.4 Hz), 4.11 (t, 2H, J=6.2 Hz), 3.24 and 3.15 (d of ABq, 2H, J=13.8 Hz), 2.95 (t, 2H, J=6.2 Hz), 2.85 (tt, 1H, J=11.6, 3.4 Hz), 2.30 (s, 3H), 2.03-1.95 (m, 2H), 1.83-1.74 (m, 2H), 1.73-1.68 (m, 1H), 1.58-1.47 (m, 1H), 1.49 (s, 3H), 1.38-1.17 (m, 4H). IR (KBr) 3400, 2937, 1735, 1614, 1513, 1328 cm−1. HRMS (ES+) m/z exact mass calcd for C29H33NO5F3 532.2311, found 532.2332.

Sources & evidence

ORD record
ord-18f7592b6875400ca597c7c9939b97a6
Source dataset
uspto-grants-2005_08
Patent number
US06930120B2

Reaction notes

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