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Sodium hydride → tert-butyl cis-3-fluoro-4-((4-(N-isobutyl-N-(5-isopropyl-3-methylpyridin-2-yl)sulfamoyl)phenoxy)methyl)piperidine-1-carboxylate

HRID 594137
ノート
印刷プレビュー

反応式

HRID 594137 の反応式
F[C:2]1[CH:7]=[CH:6][C:5]([S:8]([N:11]([CH2:22][CH:23]([CH3:25])[CH3:24])[C:12]2[C:17]([CH3:18])=[CH:16][C:15]([CH:19]([CH3:21])[CH3:20])=[CH:14][N:13]=2)(=[O:10])=[O:9])=[CH:4][CH:3]=1.[H-].[Na+].[F:28][C@H:29]1[C@@H:34]([CH2:35][OH:36])[CH2:33][CH2:32][N:31]([C:37]([O:39][C:40]([CH3:43])([CH3:42])[CH3:41])=[O:38])[CH2:30]1>CN(C)C=O>[F:28][C@H:29]1[C@@H:34]([CH2:35][O:36][C:2]2[CH:7]=[CH:6][C:5]([S:8](=[O:9])(=[O:10])[N:11]([CH2:22][CH:23]([CH3:25])[CH3:24])[C:12]3[C:17]([CH3:18])=[CH:16][C:15]([CH:19]([CH3:20])[CH3:21])=[CH:14][N:13]=3)=[CH:4][CH:3]=2)[CH2:33][CH2:32][N:31]([C:37]([O:39][C:40]([CH3:43])([CH3:42])[CH3:41])=[O:38])[CH2:30]1
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 24758Sodium hydrideHCID 89875921(3S,4R)-rel-tert-Butyl 3-fluoro-4-(hydroxymethyl)piperidine-1-carboxylateHCID 898761814-fluoro-N-isobutyl-N-(5-isopropyl-3-methylpyridin-2-yl)benzenesulfonamide

生成物 1

HCID 117925923tert-butyl cis-3-fluoro-4-((4-(N-isobutyl-N-(5-isopropyl-3-methylpyridin-2-yl)sulfamoyl)phenoxy)methyl)piperidine-1-carboxylate収率 91.7%

試薬・触媒・溶媒 1

HCID 6228
Dimethylformamide
溶媒

実験手順

4-fluoro-N-isobutyl-N-(5-isopropyl-3-methylpyridin-2-yl)benzenesulfonamide (35 mg, 0.10 mmol) was dissolved in N,N-dimethylformamide (DMF) (3 mL) and to this solution was added sodium hydride (2 mg, 0.10 mmol, 60% wt in mineral oil) followed by tert-butyl cis-3-fluoro-4-(hydroxymethyl)piperidine-1-carboxylate (22 mg, 0.10 mmol). The reaction was stirred overnight at room temperature, under nitrogen, then quenched with water and concentrated in vacuo. The crude product was extracted to the organic phase of an aqueous workup between ethyl acetate and water. The organic phase was then passed through a hydrophobic frit and concentrated in vacuo to give the title compound (53 mg). LCMS (2 min, formic) Rt 1.53 min, m/z (ES+) 578 (M+H).

後処理

  1. customquenched with water
  2. concentrationconcentrated in vacuo
  3. extractionThe crude product was extracted to the organic phase of an aqueous workup between ethyl acetate and water
  4. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-69a5669a66b64471b3e17ca4845e6759
出典データセット
uspto-grants-2016_01
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09242972B2

反応ノート

読み込み中…

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