HRID2355887

反应详情

EQUATION

反应方程式

REACTANTS

反应物

HCID10796

Cesium carbonate

CCs2O3

HCID3607724

4-Benzyloxy-2-(1H)-pyridone

C12H11NO2

结构：C=C(C(=O)OC)N(C(=O)OC(C)(C)C)C(=O)OC(C)(C)C

HCID10870342

未命名化合物

PRODUCTS

生成物

结构：COC(=O)C(Cn1ccc(OCc2ccccc2)cc1=O)N(C(=O)OC(C)(C)C)C(=O)OC(C)(C)C

HCID58864469

未命名化合物

AUXILIARIES

试剂、催化剂与溶剂

溶剂HCID6342

Acetonitrile

C2H3N

CONDITIONS

反应条件

温度: 80 °C

PROCEDURE

实验过程

To a solution of 2-(di-tert-butoxycarbonylamino)-acrylic acid methyl ester (900 mg, 3.0 mmol), and 4-benzyloxy-1H-pyridin-2-one (630 mg, 1.03 equiv) in acetonitrile (2.5 mL) was added cesium carbonate (100 mg, 0.10 equiv). The resulting suspension was heated to 80° C. via microwave for 2 h. The reaction was concentrated, dissolved in water, and extracted with methylene chloride (3×). The combined organic phases were washed with brine, dried over magnesium sulfate, and concentrated to give 1.47 g (97%) which was used without purification. Mass spec.: 503.56 (MH)+.

WORKUP

后处理

concentrationThe reaction was concentrated
dissolutiondissolved in water
extractionextracted with methylene chloride (3×)
washThe combined organic phases were washed with brine
dry with materialdried over magnesium sulfate
concentrationconcentrated
customto give 1.47 g (97%) which
customwas used without purification

来源与证据

来源类型: Open Reaction Database
ORD 记录: ord-79641440c345421e918459a7951cfbcc
来源数据集: uspto-grants-2010_07
DOI: 10.6084/m9.figshare.5104873.v1
专利: US07754732B2
来源说明: uspto-grants-2010_07

反应 SMILES

[CH3:1][O:2][C:3](=[O:21])[C:4]([N:6]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8])=[CH2:5].[CH2:22]([O:29][C:30]1[CH:35]=[CH:34][NH:33][C:32](=[O:36])[CH:31]=1)[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>C(#N)C>[CH3:1][O:2][C:3](=[O:21])[CH:4]([N:6]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8])[CH2:5][N:33]1[CH:34]=[CH:35][C:30]([O:29][CH2:22][C:23]2[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=2)=[CH:31][C:32]1=[O:36]