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 1097075Notes

Reaction equation

HRID 1097075 reaction equation
[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

Participants

4

Reactant 2

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

Product 1

HCID 66781823[4-({3-[4-(Biphenyl-2-ylcarbamoyloxy)piperidin-1-yl]propionyl}methylamino)phenyl]acetic Acid Methyl EsterYield 71.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

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.

Workup

  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)

Sources & evidence

ORD record
ord-55be88469ee14cd584f678ca92a9d6d8
Source dataset
uspto-grants-2012_03
Patent number
US08138345B2

Reaction notes

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