Hydrochloric Acid → 3-Carboxymethyl-6-benzyl-2,5-diketopiperazine

HRID 868716Notes

Reaction equation

HRID 868716 reaction equation
C[O:2][C:3](=[O:20])[CH2:4][CH:5]1[C:10](=[O:11])[NH:9][CH:8]([CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[C:7](=[O:19])[NH:6]1.[OH-].[Na+].Cl>CO>[CH2:12]([CH:8]1[C:7](=[O:19])[NH:6][CH:5]([CH2:4][C:3]([OH:20])=[O:2])[C:10](=[O:11])[NH:9]1)[C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 138837735-Benzyl-3,6-dioxo-2-piperazine acetic acid methyl ester

Product 1

HCID 1194943-Carboxymethyl-6-benzyl-2,5-diketopiperazine

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

In 1,000 l of a 50% aqueous methanol solution was suspended 55 g of the 5-benzyl-3,6-dioxo-2-piperazine acetic acid methyl ester obtained in Example 1, and 42 g of a 20% aqueous sodium hydroxide solution was added to the suspension at room temperature under stirring. Then, the hydrolysis was conducted at room temperature for two hours to form an aqueous solution. Thereafter, conc. hydrochloric acid was added dropwise to the aqueous solution, which had been removed with methanol under reduced pressure by distillation, to adjust its pH at 1. The resulting mixture was stirred at room temperature for one hour and the crystal thereby deposited was filtered, washed with water and dried to obtain 5-benzyl-3,6-dioxo-2-piperazine acetic acid.

Workup

  1. additionwas added to the suspension at room temperature
  2. customto form an aqueous solution
  3. customhad been removed with methanol under reduced pressure by distillation
  4. stirringThe resulting mixture was stirred at room temperature for one hour
  5. filtrationthe crystal thereby deposited was filtered
  6. washwashed with water
  7. customdried

Sources & evidence

ORD record
ord-cafdf8457e794dab9ea640a7878cba54
Source dataset
uspto-grants-1988_10
Patent number
US04780561

Reaction notes

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