Sodium Hydroxide → N-(2-(3-benzyl-2-(methylamino)-2,3-dihydro-1H-inden-5-yloxy)ethyl)-1-methyl-1H-imidazole-4-sulfonamide

HRID 82887ノート

反応式

HRID 82887 の反応式
[CH2:1]([CH:8]1[C:16]2[C:11](=[CH:12][CH:13]=[C:14]([O:17][CH2:18][CH2:19][NH:20][S:21]([C:24]3[N:25]=[CH:26][N:27]([CH3:29])[CH:28]=3)(=[O:23])=[O:22])[CH:15]=2)[CH2:10][CH:9]1[NH:30][C:31](=O)OCC)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-].[OH-].[Na+]>O1CCCC1>[CH2:1]([CH:8]1[C:16]2[C:11](=[CH:12][CH:13]=[C:14]([O:17][CH2:18][CH2:19][NH:20][S:21]([C:24]3[N:25]=[CH:26][N:27]([CH3:29])[CH:28]=3)(=[O:23])=[O:22])[CH:15]=2)[CH2:10][CH:9]1[NH:30][CH3:31])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

参加物

5

反応物 3

HCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 56837048ethyl 1-benzyl-6-(2-(1-methyl-1H-imidazole-4-sulfonamido)ethoxy)-2,3-dihydro-1H-inden-2-ylcarbamate

生成物 1

HCID 56642612N-(2-(3-benzyl-2-(methylamino)-2,3-dihydro-1H-inden-5-yloxy)ethyl)-1-methyl-1H-imidazole-4-sulfonamide

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

To ethyl 1-benzyl-6-(2-(1-methyl-1H-imidazole-4-sulfonamido)ethoxy)-2,3-dihydro-1H-inden-2-ylcarbamate (23.8 mg, 0.048 mmol; see example 195) in tetrahydrofuran (1 ml) was added lithium aluminium hydride in tetrahydrofuran (0.143 ml, 0.143 mmol) and the reaction mixture was refluxed for 2 h. Cooled down to room temperature and a 2N sodium hydroxide was slowly added and extracted twice with dichloromethane, washed with sodium bicarbonate and brine, dried, filtered and evaporated to obtain the crude material as white solid, that was purified by flash silica gel chromatography on 4 g SiO2-cartridge using 10% methanol in dichloromethane over 25 min to afford N-(2-(3-benzyl-2-(methylamino)-2,3-dihydro-1H-inden-5-yloxy)ethyl)-1-methyl-1H-imidazole-4-sulfonamide as a clear glass. m=6.4 mg (23%)

後処理

  1. temperaturethe reaction mixture was refluxed for 2 h
  2. extractionextracted twice with dichloromethane
  3. washwashed with sodium bicarbonate and brine
  4. customdried
  5. filtrationfiltered
  6. customevaporated
  7. customto obtain the crude material as white solid, that
  8. customwas purified by flash silica gel chromatography on 4 g SiO2-cartridge
  9. customover 25 min

出典と根拠

ORDレコード
ord-9c93dc998ed241dbba34b64fa4bde435
出典データセット
uspto-grants-2014_09
特許番号
US08846743B2

反応ノート

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