Sodium hydride → 4-benzyloxycarbonyl-1-[3-(benzhydrylidene-amino)-4-cyano-benzyl]-3-(S)-(2-methylsulfanyl-ethyl)-piperazin-2-one

HRID 1433058노트

반응식

HRID 1433058 반응식
[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.[H-].[Na+].[C:24](=[N:37][C:38]1[CH:45]=[C:44]([CH2:46]Br)[CH:43]=[CH:42][C:39]=1[C:40]#[N:41])([C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1>CN(C=O)C.C([O-])(=O)C>[CH2:1]([O:8][C:9]([N:11]1[CH2:16][CH2:15][N:14]([CH2:46][C:44]2[CH:43]=[CH:42][C:39]([C:40]#[N:41])=[C:38]([N:37]=[C:24]([C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)[C:31]3[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=3)[CH:45]=2)[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

6

반응물 3

HCID 24758Sodium hydrideHCID 179851902-(Benzhydrylideneamino)-4-bromomethylbenzonitrileHCID 670141654-Benzyloxycarbonyl-3-(S)-(2-methylsulfanyl-ethyl)-piperazin-2-one

생성물 1

HCID 865925564-benzyloxycarbonyl-1-[3-(benzhydrylidene-amino)-4-cyano-benzyl]-3-(S)-(2-methylsulfanyl-ethyl)-piperazin-2-one수율 80%

시약·촉매·용매 2

HCID 175Acetate용매HCID 6228Dimethylformamide용매2회

실험 절차

To a solution of 4-benzyloxycarbonyl-3-(S)-(2-methylsulfanyl-ethyl)-piperazin-2-one (1.15 g, 3.74 mmol) in 10 ml of DMF is added at 0° C. sodium hydride (164 mg at 60% in oil, 4.12 mmol). The solution is stirred 10 minutes then 2-(benzhydrylidene-amino)-4-bromomethyl-benzonitrile (2.6 g at 52%, 3.74 mmol) in 25 ml of DMF is added dropwise. The resulting mixture is stirred for 20 hours at room temperature, diluted with ethyle acetate, washed with water, 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 2% MeOH:CH2Cl2. The title compound (1.8 g, 80% yield) is obtained as a viscous oil.

후처리

  1. stirringThe resulting mixture is stirred for 20 hours at room temperature
  2. washwashed with water, with a saturated aqueous NaHCO3 solution, brine
  3. dry with materialThe solution is dried over MgSO4
  4. concentrationconcentrated
  5. customThe resulting crude product is purified by column chromatography on silica gel eluting with 2% MeOH

출처 및 근거

ORD 기록
ord-75b33e8dea9148acab46c57be5d0ab9c
출처 데이터셋
uspto-grants-2009_11
특허 번호
US07612075B2

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