(R)-(+)-叔丁基亚磺酰胺 → (NE,R)-N-[[4-(1,1-difluoroethyl)-2-fluorophenyl]methylidene]-2-methylpropane-2-sulfinamide

HRID 57461

反应方程式

HRID 57461 反应方程式
[F:1][C:2]([C:5]1[CH:12]=[CH:11][C:8]([CH:9]=O)=[C:7]([F:13])[CH:6]=1)([F:4])[CH3:3].[CH3:14][C:15]([S@:18]([NH2:20])=[O:19])([CH3:17])[CH3:16]>ClCCCl.S([O-])([O-])(=O)=O.[Cu+2]>[F:1][C:2]([C:5]1[CH:12]=[CH:11][C:8](/[CH:9]=[N:20]/[S@@:18]([C:15]([CH3:17])([CH3:16])[CH3:14])=[O:19])=[C:7]([F:13])[CH:6]=1)([F:4])[CH3:3]

参与物

5

反应物 2

HCID 10964479(R)-(+)-叔丁基亚磺酰胺HCID 904147854-(1,1-Difluoroethyl)-2-fluorobenzaldehyde

产物 1

HCID 90414196(NE,R)-N-[[4-(1,1-difluoroethyl)-2-fluorophenyl]methylidene]-2-methylpropane-2-sulfinamide收率 46.3%

试剂、催化剂与溶剂 2

HCID 24462HCC38 CELLS|人乳腺导管癌贴壁细胞催化剂HCID 111,2-二氯乙烷溶剂

反应条件

温度
55 °C

实验过程

To a mixture of 4-(1,1-difluoroethyl)-2-fluorobenzaldehyde (693 mg, from Step 4) and (R)-2-methylpropane-2-sulfinamide (513 mg, 4.24 mmol) in DCE (12.9 mL) was added copper(II) sulfate (882 mg, 5.52 mmol). The reaction mixture was placed in a pre-heated oil bath (55° C.) and heated for ˜2 d. The mixture was allowed to cool to room temperature, filtered through a pad of celite and rinsed with DCE. The combined filtrates were concentrated under reduced pressure. The residue was purified by column chromatography [SiO2, 24 g, heptane/ethyl acetate] providing (R,E)-N-(4-(1,1-difluoroethyl)-2-fluorobenzylidene)-2-methylpropane-2-sulfinamide (497 mg) as a yellow oil. LCMS m/z 292.1 (M+H)+, Rt 0.97 min.

后处理

  1. customThe reaction mixture was placed in a pre-heated oil bath
  2. temperatureto cool to room temperature
  3. filtrationfiltered through a pad of celite
  4. washrinsed with DCE
  5. concentrationThe combined filtrates were concentrated under reduced pressure
  6. customThe residue was purified by column chromatography [SiO2, 24 g, heptane/ethyl acetate]

来源与证据

ORD记录
ord-574f6ecd80b143f8b47b401ea8b0dd74
来源数据集
uspto-grants-2016_09
专利号
US09434719B2

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