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重氮甲烷 → rel-(3S,5S)-trans-7-Chloro-5-(2-cyclopropylethenyl)-1,5-dihydro-3-cyclopropyl-5-(trifluoromethyl)-4,1-benzoxazepin-2(3H)-one

HRID 369752
笔记
打印预览

反应方程式

HRID 369752 反应方程式
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[NH:11][C:10](=[O:12])[C@H:9]([CH:13]=[CH2:14])[O:8][C@:7](/[CH:19]=[CH:20]/[CH:21]3[CH2:23][CH2:22]3)([C:15]([F:18])([F:17])[F:16])[C:6]=2[CH:24]=1.[N+](=[CH2:27])=[N-]>CCOCC.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[NH:11][C:10](=[O:12])[C@H:9]([CH:13]3[CH2:27][CH2:14]3)[O:8][C@:7](/[CH:19]=[CH:20]/[CH:21]3[CH2:23][CH2:22]3)([C:15]([F:16])([F:17])[F:18])[C:6]=2[CH:24]=1
参与物实验过程后处理来源与证据反应笔记

参与物

5

反应物 2

HCID 9550重氮甲烷HCID 66923228rel-(3S,5S)-trans-7-Chloro-5-(2-cyclopropylethenyl)-1,5-dihydro-3-ethenyl-5-(trifluoromethyl)-4,1-benzoxazepin-2(3H)-one

产物 1

HCID 66923236rel-(3S,5S)-trans-7-Chloro-5-(2-cyclopropylethenyl)-1,5-dihydro-3-cyclopropyl-5-(trifluoromethyl)-4,1-benzoxazepin-2(3H)-one收率 62%

试剂、催化剂与溶剂 2

HCID 167845乙酸钯(Ⅱ)催化剂
HCID 3283
乙醚
溶剂
2 次

实验过程

To a solution of 73 mg of rel-(3S,5S)-trans-7-chloro-5-(2-cyclopropylethenyl)-1,5-dihydro-3-ethenyl-5-(trifluoromethyl)-4,1-benzoxazepin-2(3H)-one (from Example 42) in 7.5 mL of anhydrous ether was added first 4 mg of palladium (II) acetate and then a solution of approximately 1.23 mmol of diazomethane in 3.5 mL of ether. After stirring 30 min at room temperature, the reaction mixture was filtered through a pad of filter-aid and he filtrate was evaporated to dryness. The crude product was purified by column chromatography over silica gel (elution with methylene chloride) to give 47 mg of the title compound as a pure solid was recrystallized from ether-hexanes to afford 31 mg: mp 143-144°; HRMS: Calcd. for C18H16NO2F3Cl (M-H)- : 370.0822. Found: 370.0801.

后处理

  1. filtrationthe reaction mixture was filtered through a pad
  2. filtrationof filter-aid
  3. customhe filtrate was evaporated to dryness
  4. customThe crude product was purified by column chromatography over silica gel (elution with methylene chloride)

来源与证据

ORD记录
ord-2fe5a49996e043eaac7af99cdec3d329
来源数据集
uspto-grants-2000_10
DOI
10.6084/m9.figshare.5104873.v1
专利号
US06140320

反应笔记

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本页导航参与物实验过程后处理来源与证据反应笔记