Potassium Hydroxide → (3-{(2R)-2-[(2R)-2-hydroxy-2-(4-hydroxyphenyl)ethylamino]propyl}-1H-indol-7-yloxy)acetic acid

HRID 1351927Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1351927
C(N(CC)[C:4](=[O:30])[CH2:5][O:6][C:7]1[CH:8]=[CH:9][CH:10]=[C:11]2[C:15]=1[NH:14][CH:13]=[C:12]2[CH2:16][C@H:17]([NH:19][CH2:20][C@H:21]([OH:29])[C:22]1[CH:27]=[CH:26][C:25]([OH:28])=[CH:24][CH:23]=1)[CH3:18])C.[OH-:33].[K+]>O.C(O)C>[OH:29][C@H:21]([C:22]1[CH:23]=[CH:24][C:25]([OH:28])=[CH:26][CH:27]=1)[CH2:20][NH:19][C@H:17]([CH3:18])[CH2:16][C:12]1[C:11]2[C:15](=[C:7]([O:6][CH2:5][C:4]([OH:33])=[O:30])[CH:8]=[CH:9][CH:10]=2)[NH:14][CH:13]=1

Komponenten

5

Edukt 2

HCID 14797Potassium HydroxideHCID 69458605N,N-diethyl-2-(3-{(2R)-2-[(2 R)-2-hydroxy-2-(4-hydroxyphenyl) ethylamino]propyl}-1H-indol-7-yl-oxy)acetamide

Produkt 1

HCID 21098824(3-{(2R)-2-[(2R)-2-hydroxy-2-(4-hydroxyphenyl)ethylamino]propyl}-1H-indol-7-yloxy)acetic acidAusbeute 68 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 702EthanolLösungsmittelHCID 962WaterLösungsmittel2×

Versuchsvorschrift

A solution of N,N-diethyl-2-(3-{(2R)-2-[(2R)-2-hydroxy-2-(4-hydroxyphenyl)ethylamino]propyl}-1H-indol-7-yloxy) acetamide (12 mg, 0.027 mmol) and potassium hydroxide (60 mg, 1.1 mmol) in water (0.5 mL) and ethanol (0.5 mL) is stirred at 60° C. for 6 hours. After cooling, the mixture is concentrated and acidified by addition of water (30 mL) and acetic acid. The resultant is purified by reversed phase column chromatography (COSMOSIL 75C18-OPN (Nacalai Tesque) (octadecyl-silica gel, particle diameter: 75 μm, hereinafter, the same), water→water/methanol=10/ 1) to give the desired (3-{(2R)-2-[(2R)-2-hydroxy-2-(4-hydroxyphenyl)ethylamino]propyl}-1H-indol-7-yloxy)acetic acid (7 mg, yield: 68%).

Aufarbeitung

  1. temperatureAfter cooling
  2. concentrationthe mixture is concentrated
  3. additionacidified by addition of water (30 mL) and acetic acid
  4. customThe resultant is purified by reversed phase column chromatography (COSMOSIL 75C18-OPN (Nacalai Tesque) (octadecyl-silica gel, particle diameter

Quellen und Nachweise

ORD-Eintrag
ord-c4943b9bf95b4bfa8e34482279f12e85
Quelldatensatz
uspto-grants-2007_05
Patentnummer
US07217724B2

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