HRID390668

反应详情

EQUATION

反应方程式

REACTANTS

反应物

HCID14798

Sodium Hydroxide

HNaO

$结构：CCCCCCCNC(=O)N(C)c1cccc(-c2ccc(/C=C(\CC)C(=O)OCC)cc2OCCCC)c1$

HCID68959502

Ethyl 2-[1-[2-butoxy-3'-(3-heptyl-1-methylureido)biphenyl-4-yl]meth-(e)-ylidene]butyrate

C32H46N2O4

PRODUCTS

生成物

$结构：CCCCCCCNC(=O)N(C)c1cccc(-c2ccc(/C=C(\CC)C(=O)O)cc2OCCCC)c1$

HCID16225010

未命名化合物

收率 76%

AUXILIARIES

试剂、催化剂与溶剂

溶剂HCID702

Ethanol

C2H6O

溶剂HCID8028

Tetrahydrofuran

C4H8O

CONDITIONS

反应条件

温度: 50 °C

PROCEDURE

实验过程

40 mg (1 mmol) of sodium hydroxide are added to a solution of 531 mg (1 mmol) of ethyl 2-[1-[2-butoxy-3′-(3-heptyl-1-methylureido)biphenyl-4-yl]meth-(E)-ylidene]butyrate in 1 mL of ethanol and 10 mL of tetrahydrofuran. The reaction mixture is heated at 50° C. for 48 hours. The reaction medium is evaporated to dryness, taken up in water, acidified with aqueous 2 N hydrochloric acid solution and extracted with ethyl acetate. The organic phases are combined, washed with water and dried over magnesium sulfate. After filtration, the solvent is evaporated off and the oil obtained is purified by chromatography on a column of silica eluted with a 60/40 heptane/ethyl acetate mixture and then precipitated from heptane. 317 mg (76%) of 2-[1-[2-butoxy-3′-(3-heptyl-1-methylureido)biphenyl-4-yl]meth-(E)-ylidene]butyric acid are obtained in the form of a white powder with a melting point of 62-64° C.

WORKUP

后处理

customThe reaction medium is evaporated to dryness
extractionextracted with ethyl acetate
washwashed with water
dry with materialdried over magnesium sulfate
filtrationAfter filtration
customthe solvent is evaporated off
customthe oil obtained
customis purified by chromatography on a column of silica
washeluted with a 60/40 heptane/ethyl acetate mixture
customprecipitated from heptane

来源与证据

来源类型: Open Reaction Database
ORD 记录: ord-bf618025ad80489eb5ee9b6e6eb6211d
来源数据集: uspto-grants-2013_02
DOI: 10.6084/m9.figshare.5104873.v1
专利: US08383652B2
来源说明: uspto-grants-2013_02

反应 SMILES

[OH-].[Na+].[CH2:3]([O:7][C:8]1[CH:13]=[C:12](/[CH:14]=[C:15](\[CH2:21][CH3:22])/[C:16]([O:18]CC)=[O:17])[CH:11]=[CH:10][C:9]=1[C:23]1[CH:28]=[CH:27][CH:26]=[C:25]([N:29]([CH3:40])[C:30]([NH:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH3:39])=[O:31])[CH:24]=1)[CH2:4][CH2:5][CH3:6]>C(O)C.O1CCCC1>[CH2:3]([O:7][C:8]1[CH:13]=[C:12](/[CH:14]=[C:15](\[CH2:21][CH3:22])/[C:16]([OH:18])=[O:17])[CH:11]=[CH:10][C:9]=1[C:23]1[CH:28]=[CH:27][CH:26]=[C:25]([N:29]([CH3:40])[C:30]([NH:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH3:39])=[O:31])[CH:24]=1)[CH2:4][CH2:5][CH3:6]