HRID627166

反应详情

EQUATION

反应方程式

REACTANTS

反应物

HCID2724141

Tetra-n-butylammonium fluoride

C16H36FN

结构：C=CCON([C@H]1CN(C(=O)OC(C)(C)C)[C@H](CO[Si](C)(C)C(C)(C)C)C=C1C(=O)N(C)C)S(=O)(=O)c1ccccc1[N+](=O)[O-]

HCID89851804

未命名化合物

2 次

PRODUCTS

生成物

结构：C=CCON([C@H]1CN(C(=O)OC(C)(C)C)[C@H](CO)C=C1C(=O)N(C)C)S(=O)(=O)c1ccccc1[N+](=O)[O-]

HCID89852042

未命名化合物

收率 90.2%

AUXILIARIES

试剂、催化剂与溶剂

溶剂HCID8028

Tetrahydrofuran

C4H8O

2 次

PROCEDURE

实验过程

(2S,5R)-tert-butyl 5-(N-(allyloxy)-2-nitrophenylsulfonamido)-2-((tert-butyldimethyl-silyloxy)methyl)-4-(dimethylcarbamoyl)-5,6-dihydropyridine-1(2H)-carboxylate (Intermediate 138, 4 g, 6.11 mmol) in THF (20 mL) was charged with nitrogen and cooled in an ice-bath. To this solution was added 1M TBAF in THF (7.33 mL, 7.33 mmol) dropwise and stirred for 1 h. The solvent was then removed and the crude product loaded onto silica gel and purified via flash chromatography (0-20% MeOH-DCM) to obtain the desired product (2.98 g, 90%) as a beige solid.

WORKUP

后处理

temperaturecooled in an ice-bath
customThe solvent was then removed
custompurified via flash chromatography (0-20% MeOH-DCM)

来源与证据

来源类型: Open Reaction Database
ORD 记录: ord-9d4c09e38c92471ebebe1c995d72f13e
来源数据集: uspto-grants-2016_04
DOI: 10.6084/m9.figshare.5104873.v1
专利: US09309245B2
来源说明: uspto-grants-2016_04

反应 SMILES

[CH2:1]([O:4][N:5]([C@H:18]1[CH2:23][N:22]([C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])[C@H:21]([CH2:31][O:32][Si](C(C)(C)C)(C)C)[CH:20]=[C:19]1[C:40](=[O:44])[N:41]([CH3:43])[CH3:42])[S:6]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[N+:15]([O-:17])=[O:16])(=[O:8])=[O:7])[CH:2]=[CH2:3].CCCC[N+](CCCC)(CCCC)CCCC.[F-]>C1COCC1>[CH2:1]([O:4][N:5]([C@H:18]1[CH2:23][N:22]([C:24]([O:26][C:27]([CH3:29])([CH3:30])[CH3:28])=[O:25])[C@H:21]([CH2:31][OH:32])[CH:20]=[C:19]1[C:40](=[O:44])[N:41]([CH3:42])[CH3:43])[S:6]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[N+:15]([O-:17])=[O:16])(=[O:8])=[O:7])[CH:2]=[CH2:3]