Hydrochloric Acid → [4-({3-[4-(Biphenyl-2-ylcarbamoyloxy)piperidin-1-yl]propionyl}methylamino)-phenyl]acetic acid

HRID 1097076Notes

Reaction equation

HRID 1097076 reaction equation
C[O:2][C:3](=[O:39])[CH2:4][C:5]1[CH:10]=[CH:9][C:8]([NH:11][CH2:12][C:13](=[O:38])[CH2:14][CH2:15][N:16]2[CH2:21][CH2:20][CH:19]([O:22][C:23](=[O:37])[NH:24][C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=3[C:31]3[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=3)[CH2:18][CH2:17]2)=[CH:7][CH:6]=1.[OH-].[Li+].Cl>C(#N)C.O>[C:26]1([C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)[CH:27]=[CH:28][CH:29]=[CH:30][C:25]=1[NH:24][C:23]([O:22][CH:19]1[CH2:18][CH2:17][N:16]([CH2:15][CH2:14][C:13]([CH2:12][NH:11][C:8]2[CH:7]=[CH:6][C:5]([CH2:4][C:3]([OH:39])=[O:2])=[CH:10][CH:9]=2)=[O:38])[CH2:21][CH2:20]1)=[O:37]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 66781823[4-({3-[4-(Biphenyl-2-ylcarbamoyloxy)piperidin-1-yl]propionyl}methylamino)phenyl]acetic Acid Methyl Ester

Product 1

HCID 66781677[4-({3-[4-(Biphenyl-2-ylcarbamoyloxy)piperidin-1-yl]propionyl}methylamino)-phenyl]acetic acidYield 86.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

A stirred solution of [4-({3-[4-(biphenyl-2-ylcarbamoyloxy)piperidin-1-yl]propionyl}methylamino)phenyl]acetic acid methyl ester (8.00 g, 15.1 mmol) and lithium hydroxide (1.81 g, 75.5 mmol) in acetonitrile (20.0 mL) and water (20.0 mL) was heated at 60° C. for 3 h. The pH of the reaction mixture was adjusted to pH 5 with aqueous hydrochloric acid (1 M) and the mixture was extracted with DCM. The organic layer was dried over sodium sulfate, filtered and concentrated under reduced pressure. The residue was purified by silica gel chromatography (0-20% MeOH in DCM) to give the title compound (6.7 g, 86% yield) as an off-white solid.

Workup

  1. extractionthe mixture was extracted with DCM
  2. dry with materialThe organic layer was dried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by silica gel chromatography (0-20% MeOH in DCM)

Sources & evidence

ORD record
ord-ca5222facfa54820a810ceca53be8235
Source dataset
uspto-grants-2012_03
Patent number
US08138345B2

Reaction notes

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