HRID361696

反应详情

EQUATION

反应方程式

REACTANTS

反应物

HCID7397

p-Toluenesulfonyl chloride

C7H7ClO2S

HCID9384

Spermine tetrahydrochloride

C10H30Cl4N4

HCID14798

Sodium Hydroxide

HNaO

PRODUCTS

生成物

结构：Cc1ccc(S(=O)(=O)N(C(CCNCCCCNCCCN)(S(=O)(=O)c2ccc(C)cc2)S(=O)(=O)c2ccc(C)cc2)S(=O)(=O)c2ccc(C)cc2)cc1

HCID23440082

未命名化合物

收率 91%

AUXILIARIES

试剂、催化剂与溶剂

溶剂HCID6344

Dichloromethane

CH2Cl2

PROCEDURE

实验过程

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 0.5 N 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. NMR (CDCl3) δ7.2-7.9 (m, 16H), 5.34 (t, 2H, J=7), 2.9-3.3 (m, 12H), 2.43 (s, 12H), 1.5-2.0 (m, 8H).

WORKUP

后处理

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

来源与证据

来源类型: Open Reaction Database
ORD 记录: ord-e931446672f747b092f6fb077bfe8fd1
来源数据集: uspto-grants-1999_02
DOI: 10.6084/m9.figshare.5104873.v1
专利: US05866613
来源说明: uspto-grants-1999_02

反应 SMILES

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]