Sodium Hydroxide → 5-(2,6-Dimethoxyphenyl)-5-((quinolin-3-ylmethyl)amino)pentanoic acid

HRID 594385

Reaction equation

HRID 594385 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([O:9][CH3:10])[C:4]=1[CH:11]([NH:19][CH2:20][C:21]1[CH:22]=[N:23][C:24]2[C:29]([CH:30]=1)=[CH:28][CH:27]=[CH:26][CH:25]=2)[CH2:12][CH2:13][CH2:14][C:15]([O:17]C)=[O:16].[OH-].[Na+]>CO>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([O:9][CH3:10])[C:4]=1[CH:11]([NH:19][CH2:20][C:21]1[CH:22]=[N:23][C:24]2[C:29]([CH:30]=1)=[CH:28][CH:27]=[CH:26][CH:25]=2)[CH2:12][CH2:13][CH2:14][C:15]([OH:17])=[O:16]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 69082480Methyl 5-(2,6-dimethoxyphenyl)-5-((quinolin-3-ylmethyl)amino)pentanoate

Product 1

HCID 690835275-(2,6-Dimethoxyphenyl)-5-((quinolin-3-ylmethyl)amino)pentanoic acid

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A yellow solution of methyl 5-(2,6-dimethoxyphenyl)-5-((quinolin-3-ylmethyl)amino)-pentanoate (1.320 g; 3.23 mmol; 1.0 equiv.) in MeOH (15 ml) was treated at rt with a solution of 1 M aq. NaOH (6.5 ml; 6.5 mmol; 2.0 equiv.). The resulting solution was further stirred at rt for 1 h45. Concentration to dryness under reduced pressure, and subsequent drying under HV afforded 5-(2,6-dimethoxyphenyl)-5-((quinolin-3-ylmethyl)amino)pentanoic acid as a beige solid. LC-MS (conditions B): tR=0.59 min.; [M+H]+: 395.36 g/mol.

Workup

  1. concentrationConcentration to dryness under reduced pressure
  2. customsubsequent drying under HV

Sources & evidence

ORD record
ord-cafdd97e5f894dfd9fc1625849f3472d
Source dataset
uspto-grants-2016_01
Patent number
US09242970B2

Linked notes

Loading…