Hydrochloric Acid → 5-Benzyl-3,6-dioxo-2-piperazine acetic acid methyl ester

HRID 868713Notes

Reaction equation

HRID 868713 reaction equation
Cl.C([NH:4][C@H:5]([C:10]([NH:12][C@H:13]([C:21]([OH:23])=O)[CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=[O:11])[CH2:6][C:7](=[O:9])[OH:8])=O.[OH-].[Na+].[CH3:26]O>>[CH3:26][O:8][C:7](=[O:9])[CH2:6][CH:5]1[C:10](=[O:11])[NH:12][CH:13]([CH2:14][C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=2)[C:21](=[O:23])[NH:4]1

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 14798Sodium HydroxideHCID 92472N-(N-Formyl-L-alpha-aspartyl)-3-phenyl-L-alanine

Product 1

HCID 138837735-Benzyl-3,6-dioxo-2-piperazine acetic acid methyl ester

Conditions

Temperature
10 °C

Procedure

To a solution having 9.6 g of hydrogen chloride dissolved in 400 ml of methanol was fed 61.6 g of N-formyl-α-L-aspartyl-L-phenylalanine and the resulting mixture was reacted at 50°-60° C. for 6 hours. The reaction solution was cooled to 10° C., added dropwise with 105.6 g of a 10% aqueous sodium hydroxide solution and then subjected to reaction at 30°-40° C. for 20 hours. Thereafter, the reaction mixture was cooled to 5° C. and the crystal thereby deposited was filtered, washed with methanol and water and dried to obtain 37.6 g of 5-benzyl-3,6-dioxo-2-piperazine acetic acid methyl ester having a melting point of 216°-217.5° C.

Workup

  1. customthe resulting mixture was reacted at 50°-60° C. for 6 hours
  2. customsubjected to reaction at 30°-40° C. for 20 hours
  3. temperatureThereafter, the reaction mixture was cooled to 5° C.
  4. filtrationthe crystal thereby deposited was filtered
  5. washwashed with methanol and water
  6. customdried

Sources & evidence

ORD record
ord-2f79148524424a2c87119dfbe23f4e47
Source dataset
uspto-grants-1988_10
Patent number
US04780561

Reaction notes

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