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

HRID 1185586Notes

Reaction equation

HRID 1185586 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][CH2:21][C@H:20]2[C:24]#[N:25])=[O:18])[C:12]2[C:7](=[CH:8][C:9]([CH3:26])=[CH:10][CH:11]=2)[N:6]=1)=[O:4].[OH-].[Na+]>C1COCC1>[C:24]([C@@H:20]1[CH2:21][CH2:22][CH2:23][N:19]1[C:17](=[O:18])[CH2:16][O:15][C:13]1[C:12]2[C:7](=[CH:8][C:9]([CH3:26])=[CH:10][CH:11]=2)[N:6]=[C:5]([C:3]([OH:4])=[O:2])[CH:14]=1)#[N:25]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 686009994-[2-((S)-2-Cyano-pyrrolidin-1-yl)-2-oxo-ethoxy]-7-methyl-quinoline-2-carboxylic acid methyl ester

Product 1

HCID 686029064-[2-((S)-2-Cyano-pyrrolidin-1-yl)-2-oxo-ethoxy]-7-methyl-quinoline-2-carboxylic acid

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 772 mg 4-[2-((S)-2-Cyano-pyrrolidin-1-yl)-2-oxo-ethoxy]-7-methyl-quinoline-2-carboxylic acid methyl ester in 10 ml THF were added 2.1 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 purified by preparative HPLC (C18 reverse phase column, elution with a water/MeCN gradient with 0.1% TFA). The fractions containing the product were lyophilized to yield the pure product. Yield: 310 mg.

Workup

  1. filtrationThe reaction mixture was filtered
  2. concentrationconcentrated
  3. customthe crude product purified by preparative HPLC (
  4. washC18 reverse phase column, elution with a water/MeCN gradient with 0.1% TFA)
  5. additionThe fractions containing the product
  6. customto yield the pure product

Sources & evidence

ORD record
ord-f2fea9bae274462a856fd100082a3d9f
Source dataset
uspto-grants-2014_03
Patent number
US08669266B2

Reaction notes

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