Benzyl 4-Hydroxybenzoate → 4-{3-[4-(2-Carboxy-2-methoxy-ethyl)-phenoxy]-propoxy}-benzoic acid benzyl ester

HRID 459135Notes

Reaction equation

HRID 459135 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.O[C:20]1[CH:35]=[CH:34][C:23]([C:24]([O:26][CH2:27][C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)=[O:25])=[CH:22][CH:21]=1>>[CH2:27]([O:26][C:24](=[O:25])[C:23]1[CH:34]=[CH:35][C:20]([O:1][CH2:2][CH2:3][CH2:4][O:5][C:6]2[CH:11]=[CH:10][C:9]([CH2:12][CH:13]([C:14]([OH:16])=[O:15])[O:17][CH3:18])=[CH:8][CH:7]=2)=[CH:21][CH:22]=1)[C:28]1[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=1

Participants

3

Reactant 2

HCID 7180Benzyl 4-HydroxybenzoateHCID 69424952(2S)-3-[4-(3-Hydroxy-propoxy)-phenyl]-2-methoxy-propionic acid

Product 1

HCID 694227714-{3-[4-(2-Carboxy-2-methoxy-ethyl)-phenoxy]-propoxy}-benzoic acid benzyl ester

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 benzyl 4-hydroxybenzoate and cleavage from the resin (Standard Procedure G) gave an oily solid.

Workup

  1. customgave an oily solid

Sources & evidence

ORD record
ord-feb7c690489a4d6cb19264406e51ac99
Source dataset
uspto-grants-2007_03
Patent number
US07192982B2

Reaction notes

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