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

HRID 1433057노트

반응식

HRID 1433057 반응식
[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

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 6344Dichloromethane용매

반응 조건

온도
0 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-9fa6259c2c104a1fb0455cd384b62185
출처 데이터셋
uspto-grants-2009_11
특허 번호
US07612075B2

반응 노트

불러오는 중…