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

HRID 1433057ノート

反応式

HRID 1433057 の反応式
[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

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

反応条件

温度
0 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-9fa6259c2c104a1fb0455cd384b62185
出典データセット
uspto-grants-2009_11
特許番号
US07612075B2

反応ノート

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