Water → HCID 57656248、化合物

HRID 911578ノート

反応式

HRID 911578 の反応式
[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH2:7]([C:11]1[S:12][C:13]2[CH:19]=[CH:18][C:17]([C:20]#[N:21])=[CH:16][C:14]=2[N:15]=1)[CH:8]([CH3:10])[CH3:9].O.[OH-].[Na+]>C1COCC1>[NH2:21][CH2:20][C:17]1[CH:18]=[CH:19][C:13]2[S:12][C:11]([CH2:7][CH:8]([CH3:9])[CH3:10])=[N:15][C:14]=2[CH:16]=1

参加物

6

反応物 4

HCID 962Water2 回HCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 66707196HCID 66707196、化合物

生成物 1

HCID 57656248HCID 57656248、化合物収率 55%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

Add lithium aluminum hydride (0.78 mL, 0.78 mmol, 1M solution in THF) to 2-isobutyl-benzothiazole-5-carbonitrile (113 mg, 0.52 mmol) in THF (5 mL) and stir for 4 h at room temperature. Add water (0.27 mL), 2N sodium hydroxide (0.27 mL) and water (0.37 mL). Filter the precipitate and wash the filtrate with brine. Dry over Na2SO4 and concentrate in vacuo. Purify the crude mixture by chromatography on silica gel eluting with hexane/EtOAc (1:1) and then 1M ammonia in methanol/dichloromethane (1:9). Purify the polar fraction by SCX chromatography to give the title compound (63 mg, 55%). MS (ES+) m/z: 221 (M+HE).

後処理

  1. filtrationFilter the precipitate
  2. washwash the filtrate with brine
  3. dry with materialDry over Na2SO4
  4. concentrationconcentrate in vacuo
  5. customPurify the crude mixture by chromatography on silica gel eluting with hexane/EtOAc (1:1)
  6. customPurify the polar fraction by SCX chromatography

出典と根拠

ORDレコード
ord-c9370d32d73f4730a8dd8cf4d6d56fbc
出典データセット
uspto-grants-2011_09
特許番号
US08022062B2

反応ノート

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