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Water → 4-(7-Benzenesulfonyl-2,3-dihydro-benzo[1,4]oxazin-4-yl)-piperidine-1-carboxylic acid tert-butyl ester

HRID 2224078
ノート
印刷プレビュー

反応式

HRID 2224078 の反応式
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([NH:14][C:15]2[CH:20]=[CH:19][C:18]([S:21]([C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)(=[O:23])=[O:22])=[CH:17][C:16]=2[O:30][CH2:31][CH2:32]Cl)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[I-].[Na+].[H-].[Na+].O>CN(C=O)C>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([N:14]2[C:15]3[CH:20]=[CH:19][C:18]([S:21]([C:24]4[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=4)(=[O:23])=[O:22])=[CH:17][C:16]=3[O:30][CH2:31][CH2:32]2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([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

6

反応物 4

HCID 962WaterHCID 5238Sodium IodideHCID 24758Sodium hydrideHCID 684332104-[4-Benzenesulfonyl-2-(2-chloro-ethoxy)-phenylamino]-piperidine-1-carboxylic acid tert-butyl ester

生成物 1

HCID 684330714-(7-Benzenesulfonyl-2,3-dihydro-benzo[1,4]oxazin-4-yl)-piperidine-1-carboxylic acid tert-butyl ester収率 68.4%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

To a solution of 4-[4-benzenesulfonyl-2-(2-chloro-ethoxy)-phenylamino]-piperidine-1-carboxylic acid tert-butyl ester (0.175 g, 0.354 mmol) in 0.500 mL anhydrous DMF was added sodium iodide (2.0 mg, cat) followed by sodium hydride (17 mg. of a 60% dispersion in mineral oil, 0.424 mmol) in 3 portions. The reaction mixture was stirred at room temperature for 2 hours, added to 50 mL water, and then extracted twice with 50 mL ethyl acetate. The organic fraction was washed with 50 mL brine, dried over sodium sulfate, then concentrated in vacuo. The resulting crude oil was purified by flash chromatography (10%-40% ethyl acetate in hexanes) to give 0.111 g (0.242 mmol, 68%) of 4-(7-benzenesulfonyl-2,3-dihydro-benzo[1,4]oxazin-4-yl)-piperidine-1-carboxylic acid tert-butyl ester.

後処理

  1. extractionextracted twice with 50 mL ethyl acetate
  2. washThe organic fraction was washed with 50 mL brine
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated in vacuo
  5. customThe resulting crude oil was purified by flash chromatography (10%-40% ethyl acetate in hexanes)

出典と根拠

ORDレコード
ord-45a7cc9b100f4fb9b7eb7e104e9a9faf
出典データセット
uspto-grants-2008_05
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07378415B2

反応ノート

読み込み中…

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