HRID420946

反应详情

EQUATION

反应方程式

REACTANTS

反应物

HCID313

Hydrochloric Acid

ClH

HCID14798

Sodium Hydroxide

HNaO

结构：CCOC(=O)Cc1c(C(=O)OCC)c2cc(Oc3ccc(C(=O)N(C)C)cn3)c(Cl)cc2n1-c1ccc(C(C)(C)C)cc1

HCID66657529

未命名化合物

PRODUCTS

生成物

结构：CC(C)(C)c1ccc(-n2c(CC(=O)O)c(C(=O)O)c3cc(Oc4ccc(C(=O)O)cn4)c(Cl)cc32)cc1

HCID66657607

未命名化合物

AUXILIARIES

试剂、催化剂与溶剂

溶剂HCID31275

1,4-Dioxane

C4H8O2

PROCEDURE

实验过程

A mixture of 1-(4-tert-butylphenyl)-6-chloro-5-(5-dimethylcarbamoyl-pyridin-2-yloxy)-2-ethoxycarbonylmethylindole-3-carboxylic acid ethyl ester (124 mg, 4.07 mmol; see step (c) above), NaOH (aq, 2 M, 1.0 mL) and dioxane (2.0 mL) was heated at reflux for 48 h, cooled, acidified to pH 2 with HCl (aq, 1 M) and extracted with EtOAc. The combined extracts were washed with H2O and brine, dried (Na2SO4), concentrated and purified by chromatography to give the title compound. Yield 40 mg (36%), mp 223-235° C.

WORKUP

后处理

temperaturewas heated
temperatureat reflux for 48 h
temperaturecooled
extractionextracted with EtOAc
washThe combined extracts were washed with H2O and brine
dry with materialdried (Na2SO4)
concentrationconcentrated
custompurified by chromatography

来源与证据

来源类型: Open Reaction Database
ORD 记录: ord-b09742d3a8a84a2da8cc7877462e1e13
来源数据集: uspto-grants-2012_01
DOI: 10.6084/m9.figshare.5104873.v1
专利: US08097623B2
来源说明: uspto-grants-2012_01

反应 SMILES

C([O:3][C:4]([C:6]1[C:14]2[C:9](=[CH:10][C:11]([Cl:27])=[C:12]([O:15][C:16]3[CH:21]=[CH:20][C:19]([C:22](=[O:26])N(C)C)=[CH:18][N:17]=3)[CH:13]=2)[N:8]([C:28]2[CH:33]=[CH:32][C:31]([C:34]([CH3:37])([CH3:36])[CH3:35])=[CH:30][CH:29]=2)[C:7]=1[CH2:38][C:39]([O:41]CC)=[O:40])=[O:5])C.[OH-:44].[Na+].Cl>O1CCOCC1>[C:34]([C:31]1[CH:30]=[CH:29][C:28]([N:8]2[C:9]3[C:14](=[CH:13][C:12]([O:15][C:16]4[CH:21]=[CH:20][C:19]([C:22]([OH:26])=[O:44])=[CH:18][N:17]=4)=[C:11]([Cl:27])[CH:10]=3)[C:6]([C:4]([OH:3])=[O:5])=[C:7]2[CH2:38][C:39]([OH:41])=[O:40])=[CH:33][CH:32]=1)([CH3:35])([CH3:36])[CH3:37]