Acetaldehyde → HCID 86632922、化合物

HRID 1628582ノート

反応式

HRID 1628582 の反応式
[NH2:1][C:2]1[C:7]2[N:8]([CH2:21][CH2:22][NH:23][C:24](=[O:30])[O:25][C:26]([CH3:29])([CH3:28])[CH3:27])[C:9]([CH:11]([C:13]3[CH:18]=[CH:17][C:16]([Cl:19])=[CH:15][C:14]=3[Cl:20])[OH:12])=[N:10][C:6]=2[CH:5]=[CH:4][CH:3]=1.[CH:31](=O)[CH3:32].[C:34](O[BH-](OC(=O)C)OC(=O)C)(=O)[CH3:35].[Na+]>CO.C(O)(=O)C.C(=O)([O-])O.[Na+].[OH-].[Na+]>[Cl:20][C:14]1[CH:15]=[C:16]([Cl:19])[CH:17]=[CH:18][C:13]=1[CH:11]([OH:12])[C:9]1[N:8]([CH2:21][CH2:22][NH:23][C:24](=[O:30])[O:25][C:26]([CH3:27])([CH3:29])[CH3:28])[C:7]2[C:2]([N:1]([CH2:31][CH3:32])[CH2:34][CH3:35])=[CH:3][CH:4]=[CH:5][C:6]=2[N:10]=1

参加物

8

反応物 3

HCID 177AcetaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 86632921HCID 86632921、化合物

生成物 1

HCID 86632922HCID 86632922、化合物収率 74%

試薬・触媒・溶媒 4

HCID 176Acetic Acid溶媒HCID 887Methanol溶媒HCID 14798Sodium Hydroxide溶媒HCID 516892Sodium Bicarbonate溶媒

実験手順

To a solution of tert-butyl (2-{7-amino-2-[(2,4-dichlorophenyl) (hydroxy)methyl]-1H-benzimidazol-1-yl}ethyl)carbamate (5.00 g, 11.1 mmol) in methanol (110 mL) and acetic acid (5.5 mL) was added acetoaldehyde (4.15 mL, 66.6 mmol) at 0° C. The resultant mixture was stirred at 0° C. for 30 min. To the reaction mixture was added sodium triacetoxyborohydride (14.1 g, 66.5 mmol) at 0° C. After the resultant mixture was stirred at room temperature for 3 h, the mixture was diluted with aqueous sodium hydrogen carbonate and 8N aqueous sodium hydroxide, and extracted with ethyl acetate. The combined organic layer was washed with water and brine, dried over sodium sulfate, filtered and concentrated in vacuo. The residue was purified by column chromatography on silica gel eluting with a 20-50% ethyl acetate/n-hexane gradient mixture to give a colorless solid (4.15 mg, 8.18 mmol, 74%).

後処理

  1. extractionextracted with ethyl acetate
  2. washThe combined organic layer was washed with water and brine
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by column chromatography on silica gel eluting with a 20-50% ethyl acetate/n-hexane gradient mixture

出典と根拠

ORDレコード
ord-31765e9c856a41ef94bf87c767e135bb
出典データセット
uspto-grants-2014_07
特許番号
US08785460B2

反応ノート

読み込み中…