HRID1944962

反应详情

EQUATION

反应方程式

REACTANTS

反应物

HCID4875

Potassium iodide

HCID81531

Diisopropylethylamine

C8H19N

结构：CC(C)(C)[Si](C)(C)O[C@@H](CN)c1ccc(O)c2[nH]c(=O)ccc12

HCID59023604

未命名化合物

结构：COc1cccc(Nc2c(C(N)=O)cnc3c(C)cc(S(=O)(=O)c4cccc(C(=O)Nc5cccc(C#CCCCBr)c5)c4)cc23)c1

HCID66988630

未命名化合物

PRODUCTS

生成物

结构：COc1cccc(Nc2c(C(N)=O)cnc3c(C)cc(S(=O)(=O)c4cccc(C(=O)Nc5cccc(C#CCCCNC[C@H](O[Si](C)(C)C(C)(C)C)c6ccc(O)c7[nH]c(=O)ccc67)c5)c4)cc23)c1

HCID86659120

未命名化合物

收率 61%

AUXILIARIES

试剂、催化剂与溶剂

溶剂HCID6228

N,N-Dimethylformamide

C3H7NO

CONDITIONS

反应条件

温度: 55 °C

PROCEDURE

实验过程

A mixture of Intermediate 98 (0.35 g, 0.48 mmol) and Intermediate 2 (0.24 g, 0.72 mmol) in DMF (4.5 mL) was treated with N,N-diisopropylethylamine (0.25 mL) and catalytic potassium iodide (50 mg). The mixture was heated for 19 hours in a 55° C. oil bath. The mixture was concentrated under reduced pressure and purified via automated flash silica gel chromatography, using a 25 g Silicycle SiliSep flash column (dichloromethane/methanol/ammonium hydroxide). Concentration of the desired fractions under reduced pressure provided the title compound as a yellow solid (0.28 g, 61%). ES/MS calcd. for C53H57N6O8SSi+ 965.4. Found m/z=965.5 (M+H)+.

WORKUP

后处理

concentrationThe mixture was concentrated under reduced pressure
custompurified via automated flash silica gel chromatography

来源与证据

来源类型: Open Reaction Database
ORD 记录: ord-0dbe599fa3dc442d91aed564f8965637
来源数据集: uspto-grants-2013_03
DOI: 10.6084/m9.figshare.5104873.v1
专利: US08394829B2
来源说明: uspto-grants-2013_03

反应 SMILES

Br[CH2:2][CH2:3][CH2:4][C:5]#[C:6][C:7]1[CH:8]=[C:9]([NH:13][C:14]([C:16]2[CH:17]=[C:18]([S:22]([C:25]3[CH:26]=[C:27]4[C:32](=[C:33]([CH3:35])[CH:34]=3)[N:31]=[CH:30][C:29]([C:36]([NH2:38])=[O:37])=[C:28]4[NH:39][C:40]3[CH:45]=[CH:44][CH:43]=[C:42]([O:46][CH3:47])[CH:41]=3)(=[O:24])=[O:23])[CH:19]=[CH:20][CH:21]=2)=[O:15])[CH:10]=[CH:11][CH:12]=1.[NH2:48][CH2:49][C@@H:50]([C:59]1[CH:68]=[CH:67][C:66]([OH:69])=[C:65]2[C:60]=1[CH:61]=[CH:62][C:63](=[O:70])[NH:64]2)[O:51][Si:52]([C:55]([CH3:58])([CH3:57])[CH3:56])([CH3:54])[CH3:53].C(N(CC)C(C)C)(C)C.[I-].[K+]>CN(C=O)C>[Si:52]([O:51][C@H:50]([C:59]1[CH:68]=[CH:67][C:66]([OH:69])=[C:65]2[C:60]=1[CH:61]=[CH:62][C:63](=[O:70])[NH:64]2)[CH2:49][NH:48][CH2:2][CH2:3][CH2:4][C:5]#[C:6][C:7]1[CH:8]=[C:9]([NH:13][C:14]([C:16]2[CH:17]=[C:18]([S:22]([C:25]3[CH:26]=[C:27]4[C:32](=[C:33]([CH3:35])[CH:34]=3)[N:31]=[CH:30][C:29]([C:36]([NH2:38])=[O:37])=[C:28]4[NH:39][C:40]3[CH:45]=[CH:44][CH:43]=[C:42]([O:46][CH3:47])[CH:41]=3)(=[O:24])=[O:23])[CH:19]=[CH:20][CH:21]=2)=[O:15])[CH:10]=[CH:11][CH:12]=1)([C:55]([CH3:58])([CH3:57])[CH3:56])([CH3:54])[CH3:53]