Sodium Hydroxide → 4-[2-((R)-3-Hydroxy-pyrrolidin-1-yl)-2-oxo-ethoxy]-7-methyl-quinoline-2-carboxylic acid

HRID 1185582Notes

Reaction equation

HRID 1185582 reaction equation
C[O:2][C:3]([C:5]1[CH:14]=[C:13]([O:15][CH2:16][C:17]([N:19]2[CH2:23][CH2:22][C@@H:21]([OH:24])[CH2:20]2)=[O:18])[C:12]2[C:7](=[CH:8][C:9]([CH3:25])=[CH:10][CH:11]=2)[N:6]=1)=[O:4].[OH-].[Na+]>C1COCC1>[OH:24][C@@H:21]1[CH2:22][CH2:23][N:19]([C:17](=[O:18])[CH2:16][O:15][C:13]2[C:12]3[C:7](=[CH:8][C:9]([CH3:25])=[CH:10][CH:11]=3)[N:6]=[C:5]([C:3]([OH:4])=[O:2])[CH:14]=2)[CH2:20]1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 685992744-[2-((R)-3-Hydroxy-pyrrolidin-1-yl)-2-oxo-ethoxy]-7-methyl-quinoline-2-carboxylic acid methyl ester

Product 1

HCID 686016924-[2-((R)-3-Hydroxy-pyrrolidin-1-yl)-2-oxo-ethoxy]-7-methyl-quinoline-2-carboxylic acid

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 996 mg 4-[2-((R)-3-Hydroxy-pyrrolidin-1-yl)-2-oxo-ethoxy]-7-methyl-quinoline-2-carboxylic acid methyl ester in 10 ml THF were added 2.8 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: 700 mg

Workup

  1. filtrationThe reaction mixture was filtered
  2. concentrationconcentrated

Sources & evidence

ORD record
ord-9eb8a03c16fc43ba992a6a3f9afb54d8
Source dataset
uspto-grants-2014_03
Patent number
US08669266B2

Reaction notes

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