Trifluoroacetic acid → 4-Benzyloxycarbonyl-3-(S)-(2-methylsulfanyl-ethyl)-piperazin-2-one

HRID 1433057Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1433057
[CH2:1]([O:8][C:9]([N:11]1[CH:16]=[CH:15][NH:14][C:13](=[O:17])[C@@H:12]1[CH2:18][CH2:19][S:20][CH3:21])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[SiH](CC)(CC)CC.C(C(O)=O)(F)(F)F>C(Cl)Cl>[CH2:1]([O:8][C:9]([N:11]1[CH2:16][CH2:15][NH:14][C:13](=[O:17])[C@@H:12]1[CH2:18][CH2:19][S:20][CH3:21])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Komponenten

5

Edukt 3

HCID 6422Trifluoroacetic acidHCID 12052TriethylsilaneHCID 690260114-benzyloxycarbonyl-3-(S)-(2-methylsulfanyl-ethyl)-3,4-dihydro-1H-pyrazine-2-one

Produkt 1

HCID 670141654-Benzyloxycarbonyl-3-(S)-(2-methylsulfanyl-ethyl)-piperazin-2-oneAusbeute 46 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

To a solution of 4-benzyloxycarbonyl-3-(S)-(2-methylsulfanyl-ethyl)-3,4-dihydro-1H-pyrazine-2-one (0.3 g, 1 mmol) in CH2Cl2 is added Et3SiH (1.57 ml, 10 mmol). The resulting solution is cooled to 0° C. and CF3CO2H (2.2 ml, 30 mmol) is added dropwise. The mixture is stirred 16 hours at room temperature, washed with a saturated aqueous NaHCO3 solution, brine. The solution is dried over MgSO4, concentrated. The resulting crude product is purified by column chromatography on silica gel eluting with a gradient of 50% AcOEt:Hexane to 100% AcOEt. The title compound (0.138 g, 46% yield) is obtained as an oil.

Aufarbeitung

  1. washwashed with a saturated aqueous NaHCO3 solution, brine
  2. dry with materialThe solution is dried over MgSO4
  3. concentrationconcentrated
  4. customThe resulting crude product is purified by column chromatography on silica gel eluting with a gradient of 50% AcOEt

Quellen und Nachweise

ORD-Eintrag
ord-9fa6259c2c104a1fb0455cd384b62185
Quelldatensatz
uspto-grants-2009_11
Patentnummer
US07612075B2

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