3-(Trifluoromethyl)phenol → (2S)-2-Methoxy-3-{4-[3-(3-trifluoromethyl-phenoxy)-propoxy]-phenyl}-propionic acid

HRID 459128Notes

Reaction equation

HRID 459128 reaction equation
[OH:1][CH2:2][CH2:3][CH2:4][O:5][C:6]1[CH:11]=[CH:10][C:9]([CH2:12][C@H:13]([O:17][CH3:18])[C:14]([OH:16])=[O:15])=[CH:8][CH:7]=1.[F:19][C:20]([F:29])([F:28])[C:21]1[CH:22]=[C:23](O)[CH:24]=[CH:25][CH:26]=1>>[CH3:18][O:17][C@@H:13]([CH2:12][C:9]1[CH:10]=[CH:11][C:6]([O:5][CH2:4][CH2:3][CH2:2][O:1][C:25]2[CH:24]=[CH:23][CH:22]=[C:21]([C:20]([F:29])([F:28])[F:19])[CH:26]=2)=[CH:7][CH:8]=1)[C:14]([OH:16])=[O:15]

Participants

3

Reactant 2

HCID 73763-(Trifluoromethyl)phenolHCID 69424952(2S)-3-[4-(3-Hydroxy-propoxy)-phenyl]-2-methoxy-propionic acid

Product 1

HCID 58822762(2S)-2-Methoxy-3-{4-[3-(3-trifluoromethyl-phenoxy)-propoxy]-phenyl}-propionic acid

Procedure

The title compound was prepared from (2S)-3-[4-(3-Hydroxy-propoxy)-phenyl]-2-methoxy-propionic acid linked to Wang's Resin Example 94, Step D) via Mitsunobu coupling with 3-trifluoromethylphenol and cleavage from the resin (Standard Procedure CG) gave an oily solid.

Workup

  1. customgave an oily solid

Sources & evidence

ORD record
ord-c6d51a23c7024a20b20baae1aa8f441a
Source dataset
uspto-grants-2007_03
Patent number
US07192982B2

Reaction notes

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