Sodium Hydroxide → sodium 1-{[(3-{[3-({4-[2-(4-carboxylatophenyl)ethyl]phenyl}carbamoyl)-4,5,6,7-tetrahydro-1-benzothiophen-2-yl]carbamoyl}phenyl)sulfonyl](methyl)amino}-1-deoxy-D-glucitol

HRID 1025470Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1025470
C[O:2][C:3]([C:5]1[CH:10]=[CH:9][C:8]([CH2:11][CH2:12][C:13]2[CH:18]=[CH:17][C:16]([NH:19][C:20]([C:22]3[C:26]4[CH2:27][CH2:28][CH2:29][CH2:30][C:25]=4[S:24][C:23]=3[NH:31][C:32]([C:34]3[CH:35]=[C:36]([S:40]([N:43]([CH3:55])[CH2:44][C@@H:45]([C@H:47]([C@@H:49]([C@@H:51]([CH2:53][OH:54])[OH:52])[OH:50])[OH:48])[OH:46])(=[O:42])=[O:41])[CH:37]=[CH:38][CH:39]=3)=[O:33])=[O:21])=[CH:15][CH:14]=2)=[CH:7][CH:6]=1)=[O:4].[OH-].[Na+:57]>C(O)C>[C:3]([C:5]1[CH:10]=[CH:9][C:8]([CH2:11][CH2:12][C:13]2[CH:14]=[CH:15][C:16]([NH:19][C:20]([C:22]3[C:26]4[CH2:27][CH2:28][CH2:29][CH2:30][C:25]=4[S:24][C:23]=3[NH:31][C:32]([C:34]3[CH:35]=[C:36]([S:40]([N:43]([CH3:55])[CH2:44][C@@H:45]([C@H:47]([C@@H:49]([C@@H:51]([CH2:53][OH:54])[OH:52])[OH:50])[OH:48])[OH:46])(=[O:41])=[O:42])[CH:37]=[CH:38][CH:39]=3)=[O:33])=[O:21])=[CH:17][CH:18]=2)=[CH:7][CH:6]=1)([O-:4])=[O:2].[Na+:57]

Komponenten

4

Edukt 2

HCID 14798Sodium HydroxideHCID 712440511-deoxy-1-[{[3-({3-[(4-{2-[4-(methoxycarbonyl)phenyl]ethyl}phenyl)carbamoyl]-4,5,6,7-tetrahydro-1-benzothiophen-2-yl}carbamoyl)phenyl]sulfonyl}(methyl)amino]-D-glucitol

Produkt 1

HCID 71238568sodium 1-{[(3-{[3-({4-[2-(4-carboxylatophenyl)ethyl]phenyl}carbamoyl)-4,5,6,7-tetrahydro-1-benzothiophen-2-yl]carbamoyl}phenyl)sulfonyl](methyl)amino}-1-deoxy-D-glucitol

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

A mixture of 250 mg of 1-deoxy-1-[{[3-({3-[(4-{2-[4-(methoxycarbonyl)phenyl]ethyl}phenyl)carbamoyl]-4,5,6,7-tetrahydro-1-benzothiophen-2-yl}carbamoyl)phenyl]sulfonyl}(methyl)amino]-D-glucitol, 1.5 mL of a 1.0 M aqueous sodium hydroxide solution, and 2.5 mL of ethanol was heated and refluxed overnight. The reaction mixture was concentrated under reduced pressure and the residue was purified by ODS silica gel column chromatography (acetonitrile-water). The product was lyophilized to obtain 33 mg of sodium 1-{[(3-{[3-({4-[2-(4-carboxylatophenyl)ethyl]phenyl}carbamoyl)-4,5,6,7-tetrahydro-1-benzothiophen-2-yl]carbamoyl}phenyl)sulfonyl](methyl)amino}-1-deoxy-D-glucitol as a yellow foamed solid.

Aufarbeitung

  1. temperaturewas heated
  2. temperaturerefluxed overnight
  3. concentrationThe reaction mixture was concentrated under reduced pressure
  4. customthe residue was purified by ODS silica gel column chromatography (acetonitrile-water)

Quellen und Nachweise

ORD-Eintrag
ord-8fcc71c26a3f4d91aa6e6ade7df89520
Quelldatensatz
uspto-grants-2014_05
Patentnummer
US08729068B2

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