Sodium Hydroxide → (S)-2-(3-Carboxypropyl)-piperazine-1,4-dicarboxylic acid di-tert-butyl ester

HRID 131411Notes

Reaction equation

HRID 131411 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH2:10][C@@H:9]1[CH2:21][CH2:22][CH2:23][C:24]([O:26]CC)=[O:25])=[O:7])([CH3:4])([CH3:3])[CH3:2].[OH-].[Na+]>CO>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:14]([O:16][C:17]([CH3:18])([CH3:19])[CH3:20])=[O:15])[CH2:10][C@@H:9]1[CH2:21][CH2:22][CH2:23][C:24]([OH:26])=[O:25])=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 58625988(S)-2-(3-ethoxycarbonylpropyl)-piperazine-1,4-dicarboxylic acid di-tert-butyl ester

Product 1

HCID 58625921(S)-2-(3-Carboxypropyl)-piperazine-1,4-dicarboxylic acid di-tert-butyl ester

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Stir a solution of (S)-2-(3-ethoxycarbonylpropyl)-piperazine-1,4-dicarboxylic acid di-tert-butyl ester (0.739 g, 1.84 mmol) in MeOH add 1.0 N NaOH (2.13 mL) and continue stirring overnight. Concentrate the mixture under reduced pressure, dilute with H2O (40 mL) and wash with Et2O (3×30 mL). Acidify the aqueous layer with 10% NaHSO4 (20 mL) and extract with EtOAc (3×50 mL). Dry the organic layer with Na2SO4 filter, concentrate under reduced pressure and place the residue under vacuum to give the title compound: white solid (0.618 g), mass spectrum (m/e):373.07 (M+H).

Workup

  1. concentrationConcentrate the mixture under reduced pressure
  2. additiondilute with H2O (40 mL)
  3. washwash with Et2O (3×30 mL)
  4. extractionextract with EtOAc (3×50 mL)
  5. dry with materialDry the organic layer with Na2SO4
  6. filtrationfilter
  7. concentrationconcentrate under reduced pressure and place the residue under vacuum

Sources & evidence

ORD record
ord-497db8590f6f4e5bbe9c769e6fef9cb4
Source dataset
uspto-grants-2008_06
Patent number
US07384934B2

Reaction notes

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