Sodium Hydroxide → 4-[2-(4-tert-Butoxycarbonyl-piperazin-1-yl)-2-oxo-ethoxy]-7-methyl-quinoline-2-carboxylic acid

HRID 1185591Notes

Reaction equation

HRID 1185591 reaction equation
C([O:3][C:4]([C:6]1[CH:15]=[C:14]([O:16][CH2:17][C:18]([N:20]2[CH2:25][CH2:24][N:23]([C:26]([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:27])[CH2:22][CH2:21]2)=[O:19])[C:13]2[C:8](=[CH:9][C:10]([CH3:33])=[CH:11][CH:12]=2)[N:7]=1)=[O:5])C.[OH-].[Na+]>C1COCC1>[C:29]([O:28][C:26]([N:23]1[CH2:22][CH2:21][N:20]([C:18](=[O:19])[CH2:17][O:16][C:14]2[C:13]3[C:8](=[CH:9][C:10]([CH3:33])=[CH:11][CH:12]=3)[N:7]=[C:6]([C:4]([OH:5])=[O:3])[CH:15]=2)[CH2:25][CH2:24]1)=[O:27])([CH3:32])([CH3:30])[CH3:31]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 685992624-[2-(4-tert-Butoxycarbonyl-piperazin-1-yl)-2-oxo-ethoxy]-7-methyl-quinoline-2-carboxylic acid ethyl ester

Product 1

HCID 686004644-[2-(4-tert-Butoxycarbonyl-piperazin-1-yl)-2-oxo-ethoxy]-7-methyl-quinoline-2-carboxylic acid

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 988 mg 4-[2-(4-tert-Butoxycarbonyl-piperazin-1-yl)-2-oxo-ethoxy]-7-methyl-quinoline-2-carboxylic acid ethyl ester in 10 ml THF were added 2.2 ml aqueous NaOH (1 M) at 0° C. After 2 h the mixture was brought to pH 4 by using Amberlite IR-120 ion exchange resin. The reaction mixture was filtered and concentrated and the crude product obtained used in the next step without further purification. Yield: 925 mg.

Workup

  1. filtrationThe reaction mixture was filtered
  2. concentrationconcentrated

Sources & evidence

ORD record
ord-f48666ee104a474ca654d0669e9ccbc3
Source dataset
uspto-grants-2014_03
Patent number
US08669266B2

Reaction notes

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