3-Methoxyphenol → 2-Methoxy-3-{3-[2-(3-methoxy-phenoxy)-ethoxy]-phenyl}-propionic acid

HRID 459374Notes

Reaction equation

HRID 459374 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([OH:9])[CH:6]=[CH:7][CH:8]=1.C[O:11][C:12](=[O:27])[CH:13]([O:25][CH3:26])[CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[C:17]([O:21][CH2:22][CH2:23]Br)[CH:16]=1.CO[C@@H](CC1C=CC(OCCCOC2C=CC=CC=2)=CC=1)C(O)=O>>[CH3:26][O:25][CH:13]([CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[C:17]([O:21][CH2:22][CH2:23][O:9][C:5]2[CH:6]=[CH:7][CH:8]=[C:3]([O:2][CH3:1])[CH:4]=2)[CH:16]=1)[C:12]([OH:11])=[O:27]

Participants

4

Reactant 3

HCID 90073-MethoxyphenolHCID 58822897(2S)-2-methoxy-3-[4-(3-phenoxy propoxy)-phenyl]-propionic acidHCID 694234133-[3-(2-Bromo-ethoxy)-phenyl]-2-methoxy-propionic acid methyl ester

Product 1

HCID 184432592-Methoxy-3-{3-[2-(3-methoxy-phenoxy)-ethoxy]-phenyl}-propionic acid

Procedure

The title compound was prepared from 3-methoxy-phenol and 3-[3-(2-bromo-ethoxy)-phenyl]-2-methoxy-propionic acid methyl ester (Example 351, Step 1) via the same procedure used for the preparation of (2S)-2-methoxy-3-[4-(3-phenoxy-propoxy)-phenyl]-propionic acid (Example 285, Step 1). The enatiomers were separated by chiral HPLC. MS (ES) for C19H22O6 [M−H]31: 345.1.

Workup

  1. customThe enatiomers were separated by chiral HPLC

Sources & evidence

ORD record
ord-f8056a3a3bf04b5697f1966bdb822454
Source dataset
uspto-grants-2007_03
Patent number
US07192982B2

Reaction notes

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