methyl O-benzyl-L-serylglycinate trifluoroacetate → 3-(Benzyloxymethyl)piperazine-2,5-dione

HRID 1972401Notes

Reaction equation

HRID 1972401 reaction equation
FC(F)(F)C(O)=O.[CH2:8]([O:15][CH2:16][C@@H:17]([C:19]([NH:21][CH2:22][C:23]([O:25]C)=O)=[O:20])[NH2:18])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1>CO.C(N(CC)CC)C>[CH2:8]([O:15][CH2:16][CH:17]1[NH:18][C:23](=[O:25])[CH2:22][NH:21][C:19]1=[O:20])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

Participants

3

Reactant 1

HCID 66584220methyl O-benzyl-L-serylglycinate trifluoroacetate

Product 1

HCID 665824363-(Benzyloxymethyl)piperazine-2,5-dioneYield 68.4%

Reagents, catalysts & solvents 1

HCID 22728368Triethylamine methanolSolvent

Procedure

A 250 ml, round-bottomed flask was charged with methyl O-benzyl-L-serylglycinate trifluoroacetate (9.37 g, 24.64 mmol) and 3:1 MeOH/triethylamine (50 mL). The mixture was then heated to reflux for 16 h. The reaction was then cooled to room temperature, concentrated, and diluted with ice cold 50% aqueous EtOH (50 mL). The resulting precipitate was collected by filtration and dried under reduced pressure to give 3-(benzyloxymethyl)piperazine-2,5-dione (3.95 g) as a white solid.

Workup

  1. temperatureThe mixture was then heated
  2. temperatureto reflux for 16 h
  3. concentrationconcentrated
  4. additiondiluted with ice cold 50% aqueous EtOH (50 mL)
  5. filtrationThe resulting precipitate was collected by filtration
  6. customdried under reduced pressure

Sources & evidence

ORD record
ord-28d1c17c80384a7698fc7ce7221edbff
Source dataset
uspto-grants-2013_04
Patent number
US08431563B2

Reaction notes

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