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

HRID 585222Notes

Reaction equation

HRID 585222 reaction equation
C([O:3][C:4](=[O:27])[C:5]([CH3:26])([O:14][C:15]1[CH:20]=[CH:19][C:18]([O:21][C:22]([F:25])([F:24])[F:23])=[CH:17][CH:16]=1)[CH2:6][C:7]1[CH:12]=[CH:11][C:10]([OH:13])=[CH:9][CH:8]=1)C.[CH3:28][C:29]1[O:33][C:32]([C:34]2[S:35][CH:36]=[CH:37][CH:38]=2)=[N:31][C:30]=1[CH2:39][CH2:40]OS(C1C=CC(C)=CC=1)(=O)=O.[K+].[Br-]>>[CH3:26][C:5]([O:14][C:15]1[CH:20]=[CH:19][C:18]([O:21][C:22]([F:25])([F:23])[F:24])=[CH:17][CH:16]=1)([CH2:6][C:7]1[CH:12]=[CH:11][C:10]([O:13][CH2:40][CH2:39][C:30]2[N:31]=[C:32]([C:34]3[S:35][CH:36]=[CH:37][CH:38]=3)[O:33][C:29]=2[CH3:28])=[CH:9][CH:8]=1)[C:4]([OH:3])=[O:27]

Participants

4

Reactant 3

HCID 253877Potassium BromideHCID 223400422-(5-Methyl-2-thiophen-2-yloxazol-4-yl)ethyl tosylateHCID 693205432-(4-Trifluoromethoxyphenoxy)-3-(4-hydroxyphenyl)-2-methyl-propionic acid ethyl ester

Product 1

HCID 223400352-Methyl-3-{4-[2-(5-methyl-2-thiophen-2-yl-oxazol-4-yl)-ethoxy]-phenyl}-2-(4-trifluoromethoxy-phenoxy)-propionic Acid

Procedure

The title compound was prepared from 3-(4-hydroxy-phenyl)-2-methyl-2-(4-trifluoromethoxy-phenoxy)-propionic acid ethyl ester and toluene-4-sulfonic acid 2-(5-methyl-2-thiophen-2-yl-oxazol-4-yl)-ethyl ester using the procedure of Example 42. 1H NMR (400 MHz, CDCl3) δ 7.70-7.67 (m, 1H), 7.41 (dd, 1H, J=5.2, 1.2 Hz), 7.17 (d, 2H, J=8.8 Hz), 7.11-7.07 (m, 3H), 6.90 (d, 2H, J=8.8 Hz), 6.83 (d, 2H, J=8.8 Hz), 4.20 (t, 2H, J=6.6 Hz), 3.25 and 3.14 (d of Abq, 2H, J=14.0 Hz), 2.99 (t, 2H, J=6.4 Hz), 2.37 (s, 3H), 1.43 (s, 3H). IR (KBr) 3600, 3000, 1727, 1611, 1504, 1265 cm−1. HRMS (ES+) m/z exact mass calcd for C27H25NO6F3S 548.1354, found 548.1362.

Sources & evidence

ORD record
ord-92f0da9ad6ed47418765e361e2d0d489
Source dataset
uspto-grants-2005_08
Patent number
US06930120B2

Reaction notes

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