4-Toluenesulfonyl chloride → Tetratosylspermine

HRID 1535035노트

반응식

HRID 1535035 반응식
Cl.Cl.Cl.Cl.[NH2:5][CH2:6][CH2:7][CH2:8][NH:9][CH2:10][CH2:11][CH2:12][CH2:13][NH:14][CH2:15][CH2:16][CH2:17][NH2:18].[OH-:19].[Na+].[C:21]1([CH3:31])[CH:26]=[CH:25][C:24]([S:27](Cl)(=[O:29])=[O:28])=[CH:23][CH:22]=1>C(Cl)Cl>[S:27]([C:17]([S:27]([C:24]1[CH:25]=[CH:26][C:21]([CH3:31])=[CH:22][CH:23]=1)(=[O:29])=[O:28])([CH2:16][CH2:15][NH:14][CH2:13][CH2:12][CH2:11][CH2:10][NH:9][CH2:8][CH2:7][CH2:6][NH2:5])[N:18]([S:27]([C:24]1[CH:25]=[CH:26][C:21]([CH3:31])=[CH:22][CH:23]=1)(=[O:29])=[O:28])[S:27]([C:24]1[CH:25]=[CH:26][C:21]([CH3:31])=[CH:22][CH:23]=1)(=[O:28])=[O:19])([C:24]1[CH:25]=[CH:26][C:21]([CH3:31])=[CH:22][CH:23]=1)(=[O:29])=[O:28]

참가 물질

5

반응물 3

HCID 73974-Toluenesulfonyl chlorideHCID 9384Spermine hydrochlorideHCID 14798Sodium Hydroxide

생성물 1

HCID 23440082Tetratosylspermine수율 91%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

To spermine tetrahydrochloride (4.53 g, 13.0 mmol) and 10% aqueous NaOH (200 mL, 132 mmol) at 0° is added dropwise p-toluene-sulfonyl chloride (9.98 g, 52.3 mmol) in CH2Cl2 with rapid stirring. After 1 hr the mixture is allowed to warm to room temperature and to stir for 2 days. The organic phase is separated and washed with 0.5N HCl, H2O, and brine, dried over Na2SO4 and purified on silica gel (450 g, 3% MeOH/CHCl3) to give 9.69 g, 91% yield of tetratosylspermine.

후처리

  1. customThe organic phase is separated
  2. washwashed with 0.5N HCl, H2O, and brine
  3. dry with materialdried over Na2SO4
  4. custompurified on silica gel (450 g, 3% MeOH/CHCl3)

출처 및 근거

ORD 기록
ord-08ae0cec8ada43f395b9ab745289cacd
출처 데이터셋
uspto-grants-1992_02
특허 번호
US05091576

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