6-Hydroxyflavanone → (2S)-2-Methoxy-3-{4-[3-(4-oxo-2-phenyl-chroman-6-yloxy)-propoxy]-phenyl}-propionic acid

HRID 459137Notes

Reaction equation

HRID 459137 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:21]=[C:22]2[C:27](=[CH:28][CH:29]=1)[O:26][CH:25]([C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)[CH2:24][C:23]2=[O:36]>>[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:20]2[CH:21]=[C:22]3[C:27](=[CH:28][CH:29]=2)[O:26][CH:25]([C:30]2[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=2)[CH2:24][C:23]3=[O:36])=[CH:7][CH:8]=1)[C:14]([OH:16])=[O:15]

Participants

3

Reactant 2

HCID 27345806-HydroxyflavanoneHCID 69424952(2S)-3-[4-(3-Hydroxy-propoxy)-phenyl]-2-methoxy-propionic acid

Product 1

HCID 58822982(2S)-2-Methoxy-3-{4-[3-(4-oxo-2-phenyl-chroman-6-yloxy)-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 6-hydroxyflavanone and cleavage from the resin (Standard Procedure G) gave an oily solid.

Workup

  1. customgave an oily solid

Sources & evidence

ORD record
ord-906f3a7a607c451ca81fa73719fc450c
Source dataset
uspto-grants-2007_03
Patent number
US07192982B2

Reaction notes

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