Diisopropylethylamine → 3-(3-Methoxybenzyl)-2,5-piperazinedione

HRID 1972548Notes

Reaction equation

HRID 1972548 reaction equation
FC(F)(F)C(O)=O.[NH2:8][CH2:9][C:10]([NH:12][C@H:13]([C:23]([O:25]CC)=O)[CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[C:17]([O:21][CH3:22])[CH:16]=1)=[O:11].CCN(C(C)C)C(C)C>CO>[CH3:22][O:21][C:17]1[CH:16]=[C:15]([CH:20]=[CH:19][CH:18]=1)[CH2:14][CH:13]1[NH:12][C:10](=[O:11])[CH2:9][NH:8][C:23]1=[O:25]

Participants

4

Reactant 2

HCID 81531DiisopropylethylamineHCID 66582605Ethyl glycyl-3-methoxyphenylalaninate trifluoroacetate

Product 1

HCID 223429193-(3-Methoxybenzyl)-2,5-piperazinedioneYield 84.8%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
75 °C

Procedure

To a 100-mL round-bottomed flask was added ethyl glycyl-3-methoxyphenylalaninate trifluoroacetate (598 mg, 2.13 mmol), Hünig's base (0.371 mL, 2.13 mmol), and MeOH (20 mL). The reaction mixture was stirred at 75° C. for 24 h. The mixture was allowed to cool to room temperature. The solid formed was collected by filtration and washed with MeOH to give 3-(3-methoxybenzyl)-2,5-piperazinedione (423 mg).

Workup

  1. temperatureto cool to room temperature
  2. customThe solid formed
  3. filtrationwas collected by filtration
  4. washwashed with MeOH

Sources & evidence

ORD record
ord-27552e873e9b4ac984dbd77f688763db
Source dataset
uspto-grants-2013_04
Patent number
US08431563B2

Reaction notes

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