Sodium Hydroxide → 2-(2-methylphenyl)-2-[4-[(2-methylpropan-2-yl)oxycarbonyl]piperazin-1-yl]acetic Acid

HRID 1376034Notes

Reaction equation

HRID 1376034 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([CH:14]([C:22]([O:24]CC)=[O:23])[C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=2[CH3:21])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[OH-].[Na+]>CCO>[C:1]([O:5][C:6]([N:8]1[CH2:9][CH2:10][N:11]([CH:14]([C:22]([OH:24])=[O:23])[C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=2[CH3:21])[CH2:12][CH2:13]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 69430358HCID 69430358, compound

Product 1

HCID 27622272-(2-methylphenyl)-2-[4-[(2-methylpropan-2-yl)oxycarbonyl]piperazin-1-yl]acetic AcidYield 86.9%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To 4-(Ethoxycarbonyl-o-tolyl-methyl)-piperazine-1-carboxylic acid tert-butyl ester (152) (0.83 g, 2.27 mmol) in EtOH (10 mL) was added NaOH (0.46 g, 11.38 mmol) and the mixture stirred at room temperature for 18 h. The reaction mixture was then concentrated to dryness. The resulting residue was taken up in H2O (100 mL) and acidified (pH=4–6) with 25% KHSO4, and the desired acid was extracted into EtOAc (100 mL). The organic phase was washed with H2O (100 mL) and brine (100 mL) and concentrated to dryness yielding 0.66 g (86%) pure product.

Workup

  1. concentrationThe reaction mixture was then concentrated to dryness
  2. extractionthe desired acid was extracted into EtOAc (100 mL)
  3. washThe organic phase was washed with H2O (100 mL) and brine (100 mL)
  4. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-442063a2bfb64fed8f8ac0623953cb47
Source dataset
uspto-grants-2007_01
Patent number
US07169777B2

Reaction notes

Loading…