Lithium Hydroxide → 2-(4-Methyl-3-oxopiperazin-1-yl)-2-phenylacetic acid

HRID 404642Notes

Reaction equation

HRID 404642 reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6][N:5]([CH:8]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[C:9]([O:11]CC)=[O:10])[CH2:4][C:3]1=[O:20].[OH-].[Li+]>C(O)C.O>[CH3:1][N:2]1[CH2:7][CH2:6][N:5]([CH:8]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[C:9]([OH:11])=[O:10])[CH2:4][C:3]1=[O:20]

Participants

5

Reactant 2

HCID 3939Lithium Hydroxide2×HCID 86688901Ethyl 2-(4-methyl-3-oxopiperazin-1-yl)-2-phenylacetate

Product 1

HCID 584907532-(4-Methyl-3-oxopiperazin-1-yl)-2-phenylacetic acidYield 76.1%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

Ethyl 2-(4-methyl-3-oxopiperazin-1-yl)-2-phenylacetate (250 mg, 0.90 mmol) was dissolved in ethanol (8.6 ml) and water (4.3 ml). Lithium hydroxide (28.2 mg, 1.18 mmol) was added and the reaction was stirred at room temperature for three days. A second portion of lithium hydroxide (4.33 mg, 0.18 mmol) was added and the reaction was stirred at room temperature for 24 hours. EtOH was evaporated and 1N HCl was added to the aqueous solution till pH 7. The water was evaporated and the residue was suspended in acetonitrile and filtered on a buckner funnel washing with acetonitrile to obtain 170 mg of desired compound as a white solid. The compound was used in the next step without any further purification.

Workup

  1. stirringthe reaction was stirred at room temperature for 24 hours
  2. customEtOH was evaporated
  3. addition1N HCl was added to the aqueous solution till pH 7
  4. customThe water was evaporated
  5. filtrationfiltered on a buckner funnel
  6. washwashing with acetonitrile

Sources & evidence

ORD record
ord-da88808140474518a6dd0622ba16c240
Source dataset
uspto-grants-2014_06
Patent number
US08748613B2

Reaction notes

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