HRID735705

反应详情

EQUATION

反应方程式

REACTANTS

反应物

HCID2724141

Tetra-n-butylammonium fluoride

C16H36FN

结构：CC(Cc1ccc(C(Nc2ccc3c(N(C(=O)OC(C)(C)C)C(=O)OC(C)(C)C)nccc3c2)C(=O)NCc2cccc([N+](=O)[O-])c2)cc1)O[Si](C)(C)C(C)(C)C

HCID57842634

未命名化合物

PRODUCTS

生成物

结构：CC(O)Cc1ccc(C(Nc2ccc3c(N(C(=O)OC(C)(C)C)C(=O)OC(C)(C)C)nccc3c2)C(=O)NCc2cccc([N+](=O)[O-])c2)cc1

HCID57842733

未命名化合物

收率 26%

AUXILIARIES

试剂、催化剂与溶剂

溶剂HCID8028

Tetrahydrofuran

C4H8O

CONDITIONS

反应条件

温度: 35 °C

PROCEDURE

实验过程

To a solution of 77E (172 mg, 0.215 mmol) in 3 mL THF, was added a solution of TBAF (1M in THF, 1 mL, 1 mmol). The mixture was stirred at 35° C. for 17 h, then concentrated. The residue was dissolved in EtOAc, washed with water (2×) and brine, dried (Na2SO4) and concentrated. Purification by flash chromatography (0 to 100% EtOAc/hexanes) afforded 38 mg (26%) of 77F as a yellow glass. MS (ESI) m/z 686.4 (M+H)+.

WORKUP

后处理

concentrationconcentrated
dissolutionThe residue was dissolved in EtOAc
washwashed with water (2×) and brine
dry with materialdried (Na2SO4)
concentrationconcentrated
customPurification by flash chromatography (0 to 100% EtOAc/hexanes)

来源与证据

来源类型: Open Reaction Database
ORD 记录: ord-0ceb246662064ed5b313039a700e59ab
来源数据集: uspto-grants-2009_09
DOI: 10.6084/m9.figshare.5104873.v1
专利: US07592331B2
来源说明: uspto-grants-2009_09

反应 SMILES

[C:1]([O:5][C:6]([N:8]([C:51]([O:53][C:54]([CH3:57])([CH3:56])[CH3:55])=[O:52])[C:9]1[C:18]2[C:13](=[CH:14][C:15]([NH:19][CH:20]([C:34]3[CH:39]=[CH:38][C:37]([CH2:40][CH:41]([O:43][Si](C(C)(C)C)(C)C)[CH3:42])=[CH:36][CH:35]=3)[C:21]([NH:23][CH2:24][C:25]3[CH:30]=[CH:29][CH:28]=[C:27]([N+:31]([O-:33])=[O:32])[CH:26]=3)=[O:22])=[CH:16][CH:17]=2)[CH:12]=[CH:11][N:10]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].CCCC[N+](CCCC)(CCCC)CCCC.[F-]>C1COCC1>[C:54]([O:53][C:51]([N:8]([C:6]([O:5][C:1]([CH3:2])([CH3:4])[CH3:3])=[O:7])[C:9]1[C:18]2[C:13](=[CH:14][C:15]([NH:19][CH:20]([C:34]3[CH:35]=[CH:36][C:37]([CH2:40][CH:41]([OH:43])[CH3:42])=[CH:38][CH:39]=3)[C:21]([NH:23][CH2:24][C:25]3[CH:30]=[CH:29][CH:28]=[C:27]([N+:31]([O-:33])=[O:32])[CH:26]=3)=[O:22])=[CH:16][CH:17]=2)[CH:12]=[CH:11][N:10]=1)=[O:52])([CH3:57])([CH3:55])[CH3:56]