Ethyl 3-(4-hydroxyphenyl)-2-methyl-2-phenoxypropionate → 3-(4-{2-[2-(3-Bromophenyl)-5-methyloxazol-4-yl]ethoxy}phenyl)-2-methyl-2-phenoxypropionic Acid Ethyl Ester

HRID 585193Notes

Reaction equation

HRID 585193 reaction equation
[CH2:1]([O:3][C:4](=[O:22])[C:5]([CH3:21])([O:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[CH2:6][C:7]1[CH:12]=[CH:11][C:10]([OH:13])=[CH:9][CH:8]=1)[CH3:2].[Br:23][C:24]1[CH:25]=[C:26]([C:30]2[O:31][C:32]([CH3:48])=[C:33]([CH2:35][CH2:36]OS(C3C=CC(C)=CC=3)(=O)=O)[N:34]=2)[CH:27]=[CH:28][CH:29]=1>CCOC(C)=O>[CH2:1]([O:3][C:4](=[O:22])[C:5]([CH3:21])([O:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[CH2:6][C:7]1[CH:12]=[CH:11][C:10]([O:13][CH2:36][CH2:35][C:33]2[N:34]=[C:30]([C:26]3[CH:27]=[CH:28][CH:29]=[C:24]([Br:23])[CH:25]=3)[O:31][C:32]=2[CH3:48])=[CH:9][CH:8]=1)[CH3:2]

Participants

4

Reactant 2

HCID 11220314Ethyl 3-(4-hydroxyphenyl)-2-methyl-2-phenoxypropionateHCID 20823121Toluene-4-sulfonic acid 2-[2-(3-bromophenyl)-5-methyloxazol-4-yl]ethyl ester

Product 1

HCID 208231403-(4-{2-[2-(3-Bromophenyl)-5-methyloxazol-4-yl]ethoxy}phenyl)-2-methyl-2-phenoxypropionic Acid Ethyl Ester

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

This compound was prepared according to the procedure in Example 1, part D, using 3-(4-hydroxyphenyl)-2-methyl-2-phenoxy-propionic acid ethyl ester (551.5 mg, 1.84 mmol) and toluene-4-sulfonic acid 2-[2-(3-bromophenyl)-5-methyloxazol-4-yl]ethyl ester (1.04 g, 2.39 mmol): Rf=0.54 in 1:4 EtOAc:hexanes; 1H NMR (400 MHz, CDCl3) δ 8.14 (s, 1H), 7.92 (d, J=8.0 Hz, 1H), 7.52 (d, J=8.0 Hz, 1H), 7.30 (t, J=7.6 Hz, 1H), 7.21 (t, J=7.6 Hz, 2H), 7.15 (d, J=8.4 Hz, 2H), 6.98-6.95 (m, 1H), 6.82 (d, J=8.4 Hz, 2H), 6.83-6.81 (m, 2H), 4.23 (t, J=6.8 Hz, 2H), 4.20 (q, J=7.6 Hz, 2H), 3.26 (d, J=14.0 Hz, 1H), 3.09 (d, J=14.0 Hz, 1H), 2.97 (t, J=7.6 Hz, 2H), 2.38 (s, 3H), 1.38 (s, 3H), 1.21 (t, J=7.6 Hz, 3H); MS (EI)=564.2 (M+H)+.

Workup

  1. customThis compound was prepared

Sources & evidence

ORD record
ord-7896a23e6e914456ac437b3cec038514
Source dataset
uspto-grants-2005_08
Patent number
US06930120B2

Reaction notes

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