化工社
首页MCP工作台Skills
首页工作台通知我的
llms.txt · MCP 指南隐私政策 · 服务条款 · 支持v1.8.0
  1. 首页
  2. /反应

1,2-二氯乙烷 → 3,5-dichloro-4-((S)-2-(3-(cyclopropylmethoxy)-4-(difluoromethoxy)phenyl)-2-((S)-3-(3-formylbenzoyl)thiazolidine-2-carbonyloxy)ethyl)pyridine 1-oxide

HRID 1754311
笔记
打印预览

反应方程式

HRID 1754311 反应方程式
[Cl:1][C:2]1[CH:3]=[N+:4]([O-:34])[CH:5]=[C:6]([Cl:33])[C:7]=1[CH2:8][C@@H:9]([C:18]1[CH:23]=[CH:22][C:21]([O:24][CH:25]([F:27])[F:26])=[C:20]([O:28][CH2:29][CH:30]2[CH2:32][CH2:31]2)[CH:19]=1)[O:10][C:11]([C@H:13]1[NH:17][CH2:16][CH2:15][S:14]1)=[O:12].[CH:35]([C:37]1[CH:38]=[C:39]([CH:43]=[CH:44][CH:45]=1)[C:40](O)=[O:41])=[O:36].C(Cl)CCl>CN(C1C=CN=CC=1)C.CN(C=O)C.Cl>[Cl:1][C:2]1[CH:3]=[N+:4]([O-:34])[CH:5]=[C:6]([Cl:33])[C:7]=1[CH2:8][C@@H:9]([C:18]1[CH:23]=[CH:22][C:21]([O:24][CH:25]([F:27])[F:26])=[C:20]([O:28][CH2:29][CH:30]2[CH2:32][CH2:31]2)[CH:19]=1)[O:10][C:11]([C@H:13]1[N:17]([C:40](=[O:41])[C:39]2[CH:43]=[CH:44][CH:45]=[C:37]([CH:35]=[O:36])[CH:38]=2)[CH2:16][CH2:15][S:14]1)=[O:12]
参与物实验过程后处理来源与证据反应笔记

参与物

7

反应物 3

HCID 111,2-二氯乙烷HCID 120773-羧基苯甲醛HCID 710925213,5-dichloro-4-((S)-2-(3-(cyclopropylmethoxy)-4-(difluoromethoxy)phenyl)-2-((S)-thiazolidine-2-carbonyloxy)ethyl)pyridine 1-oxide

产物 1

HCID 867202713,5-dichloro-4-((S)-2-(3-(cyclopropylmethoxy)-4-(difluoromethoxy)phenyl)-2-((S)-3-(3-formylbenzoyl)thiazolidine-2-carbonyloxy)ethyl)pyridine 1-oxide收率 41.6%

试剂、催化剂与溶剂 3

HCID 14284
4-二甲氨基吡啶(DMAP)
催化剂
HCID 313盐酸溶剂
HCID 6228N,N-二甲基甲酰胺溶剂

实验过程

3,5-dichloro-4-((S)-2-(3-(cyclopropylmethoxy)-4-(difluoromethoxy)phenyl)-2-((S)-thiazolidine-2-carbonyloxy)ethyl)pyridine 1-oxide (Int 4, 208 mg, 0.389 mmol), 3-formylbenzoic acid (87 mg, 0.583 mmol), EDC (149 mg, 0.777 mmol), and DMAP (57.0 mg, 0.466 mmol) were dissolved in DMF (2 ml). The reaction was stirred at RT for 8 hours to achieve completion. The reaction mixture was diluted with HCl 1N, and the precipitate was filtered, washed with HCl 1N, dissolved in DCM and extracted with HCl 1N, Na2CO3 sat and brine. The organic phase was dried over Na2SO4 and concentrated under vacuum to give 3,5-dichloro-4-((S)-2-(3-(cyclopropylmethoxy)-4-(difluoromethoxy)phenyl)-2-((S)-3-(3-formylbenzoyl)thiazolidine-2-carbonyloxy)ethyl)pyridine 1-oxide (108 mg, 0.162 mmol, 41.6% yield). The compound was used in the next step without any further purification.

后处理

  1. filtrationthe precipitate was filtered
  2. washwashed with HCl 1N
  3. dissolutiondissolved in DCM
  4. extractionextracted with HCl 1N, Na2CO3
  5. dry with materialThe organic phase was dried over Na2SO4
  6. concentrationconcentrated under vacuum

来源与证据

ORD记录
ord-2bda27c8398448e7b92a363a028c282e
来源数据集
uspto-grants-2015_10
DOI
10.6084/m9.figshare.5104873.v1
专利号
US09169245B2

反应笔记

加载中…

本页导航参与物实验过程后处理来源与证据反应笔记