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Ammonium Chloride → (NE,R)-N-[2-[tert-butyl(dimethyl)silyl]oxy-1-(3-fluorophenyl)ethylidene]-2-methylpropane-2-sulfinamide

HRID 1051355
ノート
印刷プレビュー

反応式

HRID 1051355 の反応式
[Si:1]([O:8][CH2:9][C:10]([C:12]1[CH:17]=[CH:16][CH:15]=[C:14]([F:18])[CH:13]=1)=O)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[CH3:19][C:20]([S@:23]([NH2:25])=[O:24])([CH3:22])[CH3:21].[NH4+].[Cl-]>C1COCC1>[Si:1]([O:8][CH2:9]/[C:10](=[N:25]/[S@@:23]([C:20]([CH3:22])([CH3:21])[CH3:19])=[O:24])/[C:12]1[CH:17]=[CH:16][CH:15]=[C:14]([F:18])[CH:13]=1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]
参加物実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

HCID 25517Ammonium ChlorideHCID 10964479tert-Butylsulfinamide, (R)-(+)-HCID 867119952-(Tert-butyldimethylsilyloxy)-1-(3-fluorophenyl)ethanone

生成物 1

HCID 89998706(NE,R)-N-[2-[tert-butyl(dimethyl)silyl]oxy-1-(3-fluorophenyl)ethylidene]-2-methylpropane-2-sulfinamide収率 49%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran
溶媒

実験手順

To a mixture of 58a (11.3 g, 42.1 mmol) and (R)-2-methylpropane-2-sulfinamide (6.60 g, 54.7 mmol) in THF (200 mL) at RT was added Ti(Oi-Pr)4 (29.9 g, 105 mmol). The reaction mixture was heated to reflux under N2 overnight. The mixture was cooled then treated with saturated NH4Cl (5.0 mL), and the insoluble material was filtered. The filtrate was dried (Na2SO4), filtered and concentrated in vacuo. The residue was purified by SiO2 chromatography eluting with petroleum ether/EtOAc gradient (60:1 to 20:1) to afford 7.6 g (49%) of (R,E)-N-(2-(tert-butyldimethylsilyloxy)-1-(3-fluorophenyl)ethylidene)-2-methylpropane-2-sulfinamide (58b) as yellow oil. LCMS (ESI) m/z: 372.2 [M+H]+.

後処理

  1. temperatureThe reaction mixture was heated
  2. temperatureto reflux under N2 overnight
  3. temperatureThe mixture was cooled
  4. filtrationthe insoluble material was filtered
  5. dry with materialThe filtrate was dried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe residue was purified by SiO2 chromatography
  9. washeluting with petroleum ether/EtOAc gradient (60:1 to 20:1)

出典と根拠

ORDレコード
ord-c83d58cb684a41f599fe22013f2c2183
出典データセット
uspto-grants-2016_07
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09388171B2

反応ノート

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