Salicylic Acid → 2-{3-[3-(2-Carboxy-2-methoxy-ethyl)-phenoxy]-propoxy}-benzoic acid

HRID 459364Notes

Reaction equation

HRID 459364 reaction equation
C[O:2][C:3](=[O:19])[CH:4]([O:17][CH3:18])[CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([O:12][CH2:13][CH2:14][CH2:15]Br)[CH:7]=1.[OH:20][C:21]1[CH:29]=[CH:28][CH:27]=[CH:26][C:22]=1[C:23]([OH:25])=[O:24].CO[C@@H](CC1C=CC(OCCCOC2C=CC=CC=2)=CC=1)C(O)=O>>[C:3]([CH:4]([O:17][CH3:18])[CH2:5][C:6]1[CH:7]=[C:8]([CH:9]=[CH:10][CH:11]=1)[O:12][CH2:13][CH2:14][CH2:15][O:20][C:21]1[CH:29]=[CH:28][CH:27]=[CH:26][C:22]=1[C:23]([OH:25])=[O:24])([OH:2])=[O:19]

Participants

4

Reactant 3

HCID 338Salicylic AcidHCID 588228613-[3-(3-Bromo-propoxy)-phenyl]-2-methoxy-propionic acid methyl esterHCID 58822897(2S)-2-methoxy-3-[4-(3-phenoxy propoxy)-phenyl]-propionic acid

Product 1

HCID 184432502-{3-[3-(2-Carboxy-2-methoxy-ethyl)-phenoxy]-propoxy}-benzoic acid

Procedure

The title compound was prepared from 3-[3-(3-bromo-propoxy)-phenyl]-2-methoxy-propionic acid methyl ester (Example 323, Step 1) and 2-hydroxy-benzoic acid 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 C20H22O7 [M+H]+: 375.2.

Workup

  1. customThe enatiomers were separated by chiral HPLC

Sources & evidence

ORD record
ord-cc5bb65285f64275a9566a751feb996b
Source dataset
uspto-grants-2007_03
Patent number
US07192982B2

Reaction notes

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