2-(5-Methyl-2-thiophen-2-yloxazol-4-yl)ethyl tosylate → 2-(4-Chlorophenoxy)-2-methyl-3-{4-[2-(5-methyl-2-thiophen-2-yl-oxazol-4-yl)-ethoxy]-phenyl}-propionic Acid

HRID 1393423Notes

Reaction equation

HRID 1393423 reaction equation
C([O:3][C:4](=[O:23])[C:5]([O:15][C:16]1[CH:21]=[CH:20][C:19]([Cl:22])=[CH:18][CH:17]=1)([CH3:14])[CH2:6][C:7]1[CH:12]=[CH:11][C:10]([OH:13])=[CH:9][CH:8]=1)C.[CH3:24][C:25]1[O:29][C:28]([C:30]2[S:31][CH:32]=[CH:33][CH:34]=2)=[N:27][C:26]=1[CH2:35][CH2:36]OS(C1C=CC(C)=CC=1)(=O)=O>>[Cl:22][C:19]1[CH:18]=[CH:17][C:16]([O:15][C:5]([CH3:14])([CH2:6][C:7]2[CH:8]=[CH:9][C:10]([O:13][CH2:36][CH2:35][C:26]3[N:27]=[C:28]([C:30]4[S:31][CH:32]=[CH:33][CH:34]=4)[O:29][C:25]=3[CH3:24])=[CH:11][CH:12]=2)[C:4]([OH:3])=[O:23])=[CH:21][CH:20]=1

Participants

3

Reactant 2

HCID 223400422-(5-Methyl-2-thiophen-2-yloxazol-4-yl)ethyl tosylateHCID 693158912-(4-Chlorophenoxy)-3-(4-hydroxyphenyl)-2-methyl-propionic acid ethyl ester

Product 1

HCID 223399972-(4-Chlorophenoxy)-2-methyl-3-{4-[2-(5-methyl-2-thiophen-2-yl-oxazol-4-yl)-ethoxy]-phenyl}-propionic Acid

Procedure

The title compound was prepared from 2-(4-chlorophenoxy)-3-(4-hydroxy-phenyl)-2-methyl-propionic acid ethyl ester and toluene-4-sulfonic acid 2-(5-methyl-2-thiophen-2-yl-oxazol-4-yl)-ethyl ester by the procedure of Example 29. 1H NMR (400 MHz, CDCl3) δ 7.59 (d, 1H, J=4.30 Hz), 7.38 (d, 1H, J=4.30 Hz), 7.20-7.16 (m, 4H), 7.06 (dd, 1H, J=8.60 Hz, 3.91 Hz), 6.83 (t, 4H, J=8.60 Hz), 4.17 (t, 2H, J=6.65 Hz), 3.23 (d, 1H, J=14.08 Hz), 3.14 (d, 1H, J=14.08 Hz), 2.97 (t, 2H, J=6.65 Hz), 2.36 (s, 3H), 1.41 (s, 3H). MS (ES+) m/z mass calcd for C26H25ClNO5S 498.12, found 498.1.

Sources & evidence

ORD record
ord-c99fa1a87d3b47c6af04f0de5bfe3cd8
Source dataset
uspto-grants-2008_03
Patent number
US07345070B2

Reaction notes

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