HRID1726096

反应详情

EQUATION

反应方程式

REACTANTS

反应物

HCID6344

Dichloromethane

CH2Cl2

HCID2724141

Tetra-n-butylammonium fluoride

C16H36FN

结构：CC(C)(C)OC(=O)n1nc(-c2cc3cc(O[Si](C)(C)C(C)(C)C)ccc3n2C(=O)OC(C)(C)C)c2cc(OCc3ccccc3)ccc21

HCID57562471

未命名化合物

PRODUCTS

生成物

结构：CC(C)(C)OC(=O)n1nc(-c2cc3cc(O)ccc3n2C(=O)OC(C)(C)C)c2cc(OCc3ccccc3)ccc21

HCID57562414

未命名化合物

收率 76.8%

AUXILIARIES

试剂、催化剂与溶剂

溶剂HCID8028

Tetrahydrofuran

C4H8O

PROCEDURE

实验过程

A solution of 13.4 g of 5-benzyloxy-3-[1-tert-butoxycarbonyl-5-(tert-butyl-dimethylsilanyloxy)-1H-indol-2-yl]indazole-1-carboxylic acid tert-butyl ester and 6.15 g of tetrabutylammonium fluoride in 140 ml of anhydrous tetrahydrofuran is stirred at ambient temperature for 30 minutes. The solvent is evaporated off under vacuum. The reaction crude is taken up with 50 ml of dichloromethane and the organic phase is washed with 2 times 25 ml of distilled water. The organic phase is dried over magnesium sulfate. After filtration and concentration under vacuum, the reaction crude is purified by flash chromatography on 450 g of 40-63 μm silica. Elution is carried out with 100% dichloromethane and then a 98/2 then 95/5 dichloromethane/methanol mixture to Obtain 8.54 g of 5-benzyloxy-3-(1-tert-butoxycarbonyl-5-hydroxy-1H-indol-2-yl)indazole-1-carboxylic acid tert-butyl ester.

WORKUP

后处理

customThe solvent is evaporated off under vacuum
customThe reaction crude
washthe organic phase is washed with 2 times 25 ml of distilled water
dry with materialThe organic phase is dried over magnesium sulfate
filtrationAfter filtration and concentration under vacuum
customthe reaction crude
customis purified by flash chromatography on 450 g of 40-63 μm silica
washElution

来源与证据

来源类型: Open Reaction Database
ORD 记录: ord-ec08c49f37c0415b8e8d5c24a89f3908
来源数据集: uspto-grants-2009_02
DOI: 10.6084/m9.figshare.5104873.v1
专利: US07491710B2
来源说明: uspto-grants-2009_02

反应 SMILES

[C:1]([O:5][C:6]([N:8]1[C:16]2[C:11](=[CH:12][C:13]([O:17][CH2:18][C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)=[CH:14][CH:15]=2)[C:10]([C:25]2[N:26]([C:42]([O:44][C:45]([CH3:48])([CH3:47])[CH3:46])=[O:43])[C:27]3[C:32]([CH:33]=2)=[CH:31][C:30]([O:34][Si](C(C)(C)C)(C)C)=[CH:29][CH:28]=3)=[N:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[F-].C([N+](CCCC)(CCCC)CCCC)CCC.ClCCl>O1CCCC1>[C:1]([O:5][C:6]([N:8]1[C:16]2[C:11](=[CH:12][C:13]([O:17][CH2:18][C:19]3[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=3)=[CH:14][CH:15]=2)[C:10]([C:25]2[N:26]([C:42]([O:44][C:45]([CH3:48])([CH3:47])[CH3:46])=[O:43])[C:27]3[C:32]([CH:33]=2)=[CH:31][C:30]([OH:34])=[CH:29][CH:28]=3)=[N:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]