HRID2284862

反应详情

EQUATION

反应方程式

REACTANTS

反应物

HCID6342

Acetonitrile

C2H3N

HCID11430

Potassium Carbonate

CK2O3

HCID2776064

Benzyl 3-bromopropyl ether

C10H13BrO

结构：CC(=O)OC[C@H]1O[C@@H](n2cc(C(=O)c3ccc(O)cc3)c3c(C)cccc32)[C@H](OC(C)=O)[C@@H](OC(C)=O)[C@@H]1OC(C)=O

HCID118045277

未命名化合物

PRODUCTS

生成物

结构：CC(=O)OC[C@H]1O[C@@H](n2cc(C(=O)c3ccc(OCCCOCc4ccccc4)cc3)c3c(C)cccc32)[C@H](OC(C)=O)[C@@H](OC(C)=O)[C@@H]1OC(C)=O

HCID118045136

未命名化合物

收率 90.8%

AUXILIARIES

试剂、催化剂与溶剂

溶剂HCID8857

Ethyl acetate

C4H8O2

CONDITIONS

反应条件

温度: 60 °C

PROCEDURE

实验过程

To a 0.5 L stirred round bottom, purged with nitrogen, charge in order: [(2R,3R,4S,5R,6R)-3,4,5-triacetoxy-6-[3-(4-hydroxybenzoyl)-4-methyl-indol-1-yl]tetrahydropyran-2-yl]methyl acetate (13.58 mmol), acetonitrile (250 mL), and potassium carbonate (67.92 mmol). To this stirred solution, at room temperature, add 3-bromopropoxymethylbenzene (27.2 mmol) and heat at 60° C. for 16 hours under nitrogen. Dilute with EtOAc (200 mL) and filter. Concentrate the filtrate and purify by flash chromatography (330 g silica gel) eluting with 2-40% EtOAc/chloroform. Concentrate the product containing fractions to give the title compound (9.0 g. 90.79%): mass spectrum (m/z): 730.4 (M+H).

WORKUP

后处理

custompurged with nitrogen
additioncharge in order
filtrationfilter
concentrationConcentrate the filtrate
custompurify by flash chromatography (330 g silica gel)
washeluting with 2-40% EtOAc/chloroform
concentrationConcentrate the product
additioncontaining fractions

来源与证据

来源类型: Open Reaction Database
ORD 记录: ord-b3dda1af553a46bf99bf37d68b5a4a5b
来源数据集: uspto-grants-2015_09
DOI: 10.6084/m9.figshare.5104873.v1
专利: US09145437B2
来源说明: uspto-grants-2015_09

反应 SMILES

[C:1]([O:4][CH2:5][C@@H:6]1[C@@H:11]([O:12][C:13](=[O:15])[CH3:14])[C@H:10]([O:16][C:17](=[O:19])[CH3:18])[C@@H:9]([O:20][C:21](=[O:23])[CH3:22])[C@H:8]([N:24]2[C:32]3[C:27](=[C:28]([CH3:33])[CH:29]=[CH:30][CH:31]=3)[C:26]([C:34](=[O:42])[C:35]3[CH:40]=[CH:39][C:38]([OH:41])=[CH:37][CH:36]=3)=[CH:25]2)[O:7]1)(=[O:3])[CH3:2].C(#N)C.C(=O)([O-])[O-].[K+].[K+].Br[CH2:53][CH2:54][CH2:55][O:56][CH2:57][C:58]1[CH:63]=[CH:62][CH:61]=[CH:60][CH:59]=1>CCOC(C)=O>[C:1]([O:4][CH2:5][C@@H:6]1[C@@H:11]([O:12][C:13](=[O:15])[CH3:14])[C@H:10]([O:16][C:17](=[O:19])[CH3:18])[C@@H:9]([O:20][C:21](=[O:23])[CH3:22])[C@H:8]([N:24]2[C:32]3[C:27](=[C:28]([CH3:33])[CH:29]=[CH:30][CH:31]=3)[C:26]([C:34](=[O:42])[C:35]3[CH:40]=[CH:39][C:38]([O:41][CH2:53][CH2:54][CH2:55][O:56][CH2:57][C:58]4[CH:63]=[CH:62][CH:61]=[CH:60][CH:59]=4)=[CH:37][CH:36]=3)=[CH:25]2)[O:7]1)(=[O:3])[CH3:2]