Biphenyl-2-ylcarbamic Acid Piperidin-4-yl Ester → [4-({3-[4-(Biphenyl-2-ylcarbamoyloxy)piperidin-1-yl]propionyl}methylamino)phenyl]acetic Acid Methyl Ester

HRID 1097075Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1097075
[CH3:1][O:2][C:3](=[O:17])[CH2:4][C:5]1[CH:10]=[CH:9][C:8]([NH:11][CH2:12][C:13](=[O:16])[CH:14]=[CH2:15])=[CH:7][CH:6]=1.[NH:18]1[CH2:23][CH2:22][CH:21]([O:24][C:25](=[O:39])[NH:26][C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=2[C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)[CH2:20][CH2:19]1>CCO>[CH3:1][O:2][C:3](=[O:17])[CH2:4][C:5]1[CH:10]=[CH:9][C:8]([NH:11][CH2:12][C:13](=[O:16])[CH2:14][CH2:15][N:18]2[CH2:19][CH2:20][CH:21]([O:24][C:25](=[O:39])[NH:26][C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=3[C:33]3[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=3)[CH2:22][CH2:23]2)=[CH:7][CH:6]=1

Komponenten

4

Edukt 2

HCID 10851461Biphenyl-2-ylcarbamic Acid Piperidin-4-yl EsterHCID 66770363[4-(Acryloylmethylamino)phenyl]acetic Acid Methyl Ester

Produkt 1

HCID 66781823[4-({3-[4-(Biphenyl-2-ylcarbamoyloxy)piperidin-1-yl]propionyl}methylamino)phenyl]acetic Acid Methyl EsterAusbeute 71,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

A stirred solution of [4-(acryloylmethylamino)phenyl]acetic acid methyl ester (˜22.3 mmol) and biphenyl-2-ylcarbamic acid piperidin-4-yl ester (6.61 g, 22.3 mmol) in EtOH (15.0 mL) was heated at reflux overnight. The reaction mixture was concentrated under reduced pressure and the residue was purified by silica gel chromatography (0-5% MeOH in DCM) to give the title compound (8.41 g, 71% yield, 2 steps) as a brown sticky solid.

Aufarbeitung

  1. temperatureat reflux overnight
  2. concentrationThe reaction mixture was concentrated under reduced pressure
  3. customthe residue was purified by silica gel chromatography (0-5% MeOH in DCM)

Quellen und Nachweise

ORD-Eintrag
ord-55be88469ee14cd584f678ca92a9d6d8
Quelldatensatz
uspto-grants-2012_03
Patentnummer
US08138345B2

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