Trifluoroacetic acid → (S)-1-Allyl-3-benzyl-6-methylenepiperazine-2,5-dione

HRID 15398Notes

Reaction equation

HRID 15398 reaction equation
C(O)(C(F)(F)F)=O.[CH2:8]([NH:11][C:12](=[O:27])[C@H:13]([CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)[NH:14][C:15](=[O:19])[C:16](=O)[CH3:17])[CH:9]=[CH2:10]>>[CH2:8]([N:11]1[C:16](=[CH2:17])[C:15](=[O:19])[NH:14][C@@H:13]([CH2:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[C:12]1=[O:27])[CH:9]=[CH2:10]

Participants

3

Reactant 2

HCID 6422Trifluoroacetic acid2×HCID 11950630HCID 11950630, compound

Product 1

HCID 11950453(S)-1-Allyl-3-benzyl-6-methylenepiperazine-2,5-dione

Procedure

The effect of the amount of TFA acid catalyst was evaluated. (S)-1-Allyl-3-benzyl-6-methylenepiperazine-2,5-dione was prepared by reacting N-2-oxo-propanoyl-L-phenylalanine allylamide with various amounts of trifluoroacetic acid for 24 hours. Enantiomeric excess of the product was determined by chiral HPLC using a CHIRALCEL OD column eluted with n-Hexane:Ethanol (5:1). The TFA amounts, product yields, and enantiometric excess presented in Table 2.

Workup

  1. customfor 24 hours
  2. washeluted with n-Hexane:Ethanol (5:1)
  3. customproduct yields

Sources & evidence

ORD record
ord-a22072adf265439da20bd058ef52816c
Source dataset
uspto-grants-2010_06
Patent number
US07732605B2

Reaction notes

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