2-((S)-6-((4-(benzyloxy)-2',6'-dimethyl-4'-(((R)-tetrahydrofuran-3-yl)oxy)biphenyl-3-yl)methoxy)-2,3-dihydrobenzofuran-3-yl)acetic acid → 2-((S)-6-((4-hydroxy-2',6'-dimethyl-4'-(((R)-tetrahydrofuran-3-yl)oxy)biphenyl-3-yl)methoxy)-2,3-dihydrobenzofuran-3-yl)acetic acid

HRID 2280688Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2280688
C([O:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[C:20]([CH3:21])=[CH:19][C:18]([O:22][C@@H:23]3[CH2:27][CH2:26][O:25][CH2:24]3)=[CH:17][C:16]=2[CH3:28])=[CH:11][C:10]=1[CH2:29][O:30][C:31]1[CH:43]=[CH:42][C:34]2[C@H:35]([CH2:38][C:39]([OH:41])=[O:40])[CH2:36][O:37][C:33]=2[CH:32]=1)C1C=CC=CC=1>C(OCC)(=O)C.[Pd]>[OH:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[C:20]([CH3:21])=[CH:19][C:18]([O:22][C@@H:23]3[CH2:27][CH2:26][O:25][CH2:24]3)=[CH:17][C:16]=2[CH3:28])=[CH:11][C:10]=1[CH2:29][O:30][C:31]1[CH:43]=[CH:42][C:34]2[C@H:35]([CH2:38][C:39]([OH:41])=[O:40])[CH2:36][O:37][C:33]=2[CH:32]=1

Komponenten

4

Edukt 1

HCID 897018032-((S)-6-((4-(benzyloxy)-2',6'-dimethyl-4'-(((R)-tetrahydrofuran-3-yl)oxy)biphenyl-3-yl)methoxy)-2,3-dihydrobenzofuran-3-yl)acetic acid

Produkt 1

HCID 716575172-((S)-6-((4-hydroxy-2',6'-dimethyl-4'-(((R)-tetrahydrofuran-3-yl)oxy)biphenyl-3-yl)methoxy)-2,3-dihydrobenzofuran-3-yl)acetic acidAusbeute 14,1 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938PalladiumKatalysatorHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

2-((S)-6-((4-(Benzyloxy)-2′,6′-dimethyl-4′-(((R)-tetrahydrofuran-3-yl)oxy)biphenyl-3-yl)methoxy)-2,3-dihydrobenzofuran-3-yl)acetic acid 36c (152 mg, 0.26 mmol) was dissolved in 5 mL of ethyl acetate, followed by addition of Pd/C (30 mg, 10%). The reaction solution was stirred for 12 hours. The resulting solution was filtered. The filtrate was concentrated under reduced pressure and the residue was purified by TLC with elution system A to obtain the crude title compound 2-((S)-6-((4-hydroxy-2′,6′-dimethyl-4′-(((R)-tetrahydrofuran-3-yl)oxy)biphenyl-3-yl)methoxy)-2,3-dihydrobenzofuran-3-yl)acetic acid 36 (18 mg, yield 14.1%) as a white solid.

Aufarbeitung

  1. filtrationThe resulting solution was filtered
  2. concentrationThe filtrate was concentrated under reduced pressure
  3. customthe residue was purified by TLC with elution system

Quellen und Nachweise

ORD-Eintrag
ord-bcaec1618eae44108da45ebbc5cc285c
Quelldatensatz
uspto-grants-2015_09
Patentnummer
US09139548B2

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