HRID494598

反应详情

EQUATION

反应方程式

REACTANTS

反应物

HCID1049

Pyridine

C5H5N

HCID31297

Methanesulfonyl chloride

CH3ClO2S

结构：CC(C)(C)CC[C@@]1(C)C(=O)C(C2=NS(=O)(=O)c3cc(N)ccc3N2)=C(O)c2ccccc21

HCID135869465

未命名化合物

PRODUCTS

生成物

结构：CC(C)(C)CC[C@@]1(C)C(=O)C(C2=NS(=O)(=O)c3cc(NS(C)(=O)=O)ccc3N2)=C(O)c2ccccc21

HCID135430231

未命名化合物

收率 87.2%

AUXILIARIES

试剂、催化剂与溶剂

溶剂HCID6344

Dichloromethane

CH2Cl2

PROCEDURE

实验过程

To a solution of the product of Example 49-6 (235.0 g, 0.518 mol) and pyridine (123.0 g, 1.55 mol) in dichloromethane (1645 mL) at 18-20° C. was added methane sulfonyl chloride (89.0 g, 0.777 mol) over 45 minutes. The solution was mixed at RT for 3.5 h then quenched with 1 M HCl (1500 mL). The layers were separated and the organic layer was concentrated under vacuum. The product was crystallized from ethyl acetate/heptane (1/1, 8 volumes) to give the title compound (240.01 g, 87%).

WORKUP

后处理

additionThe solution was mixed at RT for 3.5 h
customthen quenched with 1 M HCl (1500 mL)
customThe layers were separated
concentrationthe organic layer was concentrated under vacuum
customThe product was crystallized from ethyl acetate/heptane (1/1, 8 volumes)

来源与证据

来源类型: Open Reaction Database
ORD 记录: ord-d948df74791f4d48a6eb68fe6b465990
来源数据集: uspto-grants-2009_05
DOI: 10.6084/m9.figshare.5104873.v1
专利: US07538105B2
来源说明: uspto-grants-2009_05

反应 SMILES

[NH2:1][C:2]1[CH:32]=[CH:31][C:5]2[NH:6][C:7]([C:12]3[C:13](=[O:30])[C@@:14]([CH2:24][CH2:25][C:26]([CH3:29])([CH3:28])[CH3:27])([CH3:23])[C:15]4[C:20]([C:21]=3[OH:22])=[CH:19][CH:18]=[CH:17][CH:16]=4)=[N:8][S:9](=[O:11])(=[O:10])[C:4]=2[CH:3]=1.N1C=CC=CC=1.[CH3:39][S:40](Cl)(=[O:42])=[O:41]>ClCCl>[CH3:29][C:26]([CH3:27])([CH3:28])[CH2:25][CH2:24][C@:14]1([CH3:23])[C:15]2[C:20](=[CH:19][CH:18]=[CH:17][CH:16]=2)[C:21]([OH:22])=[C:12]([C:7]2[NH:6][C:5]3[CH:31]=[CH:32][C:2]([NH:1][S:40]([CH3:39])(=[O:42])=[O:41])=[CH:3][C:4]=3[S:9](=[O:11])(=[O:10])[N:8]=2)[C:13]1=[O:30]