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Cesium fluoride → tert-Butyl 4-(4-(3-(cyclopropylmethyl)ureido)phenoxy)piperidine-1-carboxylate

HRID 515270
ノート
印刷プレビュー

反応式

HRID 515270 の反応式
[CH:1]1([CH2:4][NH:5][C:6]([NH:8][C:9]2[CH:14]=[CH:13][C:12]([OH:15])=[CH:11][CH:10]=2)=[O:7])[CH2:3][CH2:2]1.[F-].[Cs+].CS(O[CH:23]1[CH2:28][CH2:27][N:26]([C:29]([O:31][C:32]([CH3:35])([CH3:34])[CH3:33])=[O:30])[CH2:25][CH2:24]1)(=O)=O>CC(N(C)C)=O>[CH:1]1([CH2:4][NH:5][C:6](=[O:7])[NH:8][C:9]2[CH:10]=[CH:11][C:12]([O:15][CH:23]3[CH2:28][CH2:27][N:26]([C:29]([O:31][C:32]([CH3:35])([CH3:34])[CH3:33])=[O:30])[CH2:25][CH2:24]3)=[CH:13][CH:14]=2)[CH2:3][CH2:2]1
参加物反応条件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 25953Cesium fluorideHCID 41848691-(tert-Butoxycarbonyl)-4-(methanesulfonyloxy)piperidineHCID 671944861-(Cyclopropylmethyl)-3-(4-hydroxyphenyl)urea

生成物 1

HCID 67193130tert-Butyl 4-(4-(3-(cyclopropylmethyl)ureido)phenoxy)piperidine-1-carboxylate

試薬・触媒・溶媒 1

HCID 31374Dimethylacetamide溶媒2 回

反応条件

温度
85 °C

実験手順

To a stirring solution of 1-(cyclopropylmethyl)-3-(4-hydroxyphenyl)urea (6.79 mmol, 1.4 g) in dimethylacetamide (50 mL) was added cesium fluoride (20.36 mmol, 3.09 g) followed by a solution of tert-butyl 4-(methylsulfonyloxy)piperidine-1-carboxylate (8.15 mmol, 2.276 g) in dimethylacetamide (50 mL). The resulting suspension was heated to 85° C. overnight. The reaction mixture was filtered and the filtrate concentrated under vacuum. The residue was dissolved in dichloromethane and washed with water. The organic layer was separated, dried over magnesium sulfate and concentrated under vacuum. The residue was dissolved in dichloromethane and purified by column chromatography (eluent 2-8% methanol in dichloromethane) to afford the title compound. MS (ESI) m/z 390.0 [M+H]+

後処理

  1. filtrationThe reaction mixture was filtered
  2. concentrationthe filtrate concentrated under vacuum
  3. dissolutionThe residue was dissolved in dichloromethane
  4. washwashed with water
  5. customThe organic layer was separated
  6. dry with materialdried over magnesium sulfate
  7. concentrationconcentrated under vacuum
  8. dissolutionThe residue was dissolved in dichloromethane
  9. custompurified by column chromatography (eluent 2-8% methanol in dichloromethane)

出典と根拠

ORDレコード
ord-a2d857227f6549dea464a5b5fcdc6da7
出典データセット
uspto-grants-2015_08
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09108939B2

反応ノート

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