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N-((1,1-dimethylethoxy)carbonyl)-beta-alanine → (S)-3-tert-Butoxycarbonylamino-1-[4-({[2-(2,3-dihydrobenzofuran-5-yl)-1-methylethyl]ethylamino}methyl)piperidin-1-yl]-propan-1-one

HRID 429831
ノート
印刷プレビュー

反応式

HRID 429831 の反応式
[C:1]([O:5][C:6]([NH:8][CH2:9][CH2:10][C:11]([OH:13])=O)=[O:7])([CH3:4])([CH3:3])[CH3:2].[O:14]1[C:18]2[CH:19]=[CH:20][C:21]([CH2:23][C@@H:24]([N:26]([CH2:29][CH:30]3[CH2:35][CH2:34][NH:33][CH2:32][CH2:31]3)[CH2:27][CH3:28])[CH3:25])=[CH:22][C:17]=2[CH2:16][CH2:15]1>ClCCl>[C:1]([O:5][C:6]([NH:8][CH2:9][CH2:10][C:11]([N:33]1[CH2:34][CH2:35][CH:30]([CH2:29][N:26]([C@@H:24]([CH3:25])[CH2:23][C:21]2[CH:20]=[CH:19][C:18]3[O:14][CH2:15][CH2:16][C:17]=3[CH:22]=2)[CH2:27][CH3:28])[CH2:31][CH2:32]1)=[O:13])=[O:7])([CH3:2])([CH3:3])[CH3:4]
参加物実験手順後処理出典と根拠反応ノート

参加物

4

反応物 2

HCID 76809N-((1,1-dimethylethoxy)carbonyl)-beta-alanineHCID 15546287(S)-N-[2-(2,3-dihydrobenzofuran-5-yl)-1-methylethyl]-N-ethyl-(piperidin-4-ylmethyl)amine

生成物 1

HCID 54233503(S)-3-tert-Butoxycarbonylamino-1-[4-({[2-(2,3-dihydrobenzofuran-5-yl)-1-methylethyl]ethylamino}methyl)piperidin-1-yl]-propan-1-one収率 97.2%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

実験手順

To a solution of N-tert-butoxycarbonyl-β-alanine (0.31 grams, 165 mmole) in dichloromethane (5 ml) was added N,N′-carbonyldiimidazole (0.3 grams, 185 mmole). The reaction mixture was stirred at room temperature for 2 hours. To the reaction mixture was added a solution of (S)-N-[2-(2,3-dihydrobenzofuran-5-yl)-1-methylethyl]-N-ethyl-(piperidine-4-ylmethyl)amine (0.5 grams, 1.65 mmole) in dichloromethane (2 ml). The reaction mixture was stirred for 16 hours. The solvent was evaporated and the residue was purified by flash chromatography on silica gel using 2% methanol in dichloromethane containing 0.1% ammonium hydroxide. Appropriate fractions were combined and concentrated to give (S)-3-tert-butoxycarbonylamino-1-[4-({[2-(2,3-dihydrobenzofuran-5-yl)-1-methylethyl]-ethylamino}methyl)piperidin-1-yl]propan-1-one as a solid (0.76 grams, 97%).

後処理

  1. stirringThe reaction mixture was stirred for 16 hours
  2. customThe solvent was evaporated
  3. customthe residue was purified by flash chromatography on silica gel using 2% methanol in dichloromethane containing 0.1% ammonium hydroxide
  4. concentrationconcentrated

出典と根拠

ORDレコード
ord-5ca099bd3998408abc74940048be0e87
出典データセット
uspto-grants-2001_11
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US06319920B1

反応ノート

読み込み中…

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