Trifluoroacetic acid → (S)-1-Benzyl-3-ethylpiperazine-2,5-dione

HRID 38274

Reaktionsgleichung

Reaktionsgleichung von HRID 38274
C1CCC(N=C=NC2CCCCC2)CC1.[NH2:16][CH:17]([CH2:21][CH3:22])[C:18](O)=[O:19].[CH2:23]([NH:30][CH2:31][C:32](OCC)=[O:33])[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1.C(O)(C(F)(F)F)=O>C(Cl)Cl>[CH2:21]([C@@H:17]1[NH:16][C:32](=[O:33])[CH2:31][N:30]([CH2:23][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[C:18]1=[O:19])[CH3:22]

Komponenten

6

Edukt 4

HCID 6422Trifluoroacetic acidHCID 6657Alpha-Aminobutyric AcidHCID 10868DicyclohexylcarbodiimideHCID 80908N-Benzylglycine ethyl ester

Produkt 1

HCID 20598791(S)-1-Benzyl-3-ethylpiperazine-2,5-dione

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

To a solution of DCC (5.07 g) in DCM (140 mL) at 0° C. was added N—BOC-L-□-aminobutyric acid (5 g) followed by ethyl JV-benzylglycinate (4.6 mL) dropwise. The resulting solution was stirred at 0° C. for 2 h and RT 1 h, filtered and the concentrated to give an oil. This was dissolved in DCM (100 mL) and TFA (100 ml) and stirred for 1 h. The solution was concentrated under reduced pressure. The residue was stirred in saturated aq NaHCO3 (125 ml) and EtOAc (125 ml) for 6 h. The organics were separated, dried (Na2SO4), and concentrated to give the sub title compound as a white solid. (5.68 g).

Aufarbeitung

  1. filtrationfiltered
  2. concentrationthe concentrated
  3. customto give an oil
  4. concentrationThe solution was concentrated under reduced pressure
  5. stirringThe residue was stirred in saturated aq NaHCO3 (125 ml)
  6. waitEtOAc (125 ml) for 6 h
  7. customThe organics were separated
  8. dry with materialdried (Na2SO4)
  9. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-1ac27f39dc7c470f9810920706515d93
Quelldatensatz
uspto-grants-2013_09
Patentnummer
US08524715B2

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