Acetaldehyde → HCID 68761561、化合物

HRID 1398754ノート

反応式

HRID 1398754 の反応式
[NH2:1][C:2]1[C:7]2[N:8]([CH2:20][CH2:21][C:22]([O:24][CH2:25][CH3:26])=[O:23])[C:9]([NH:11][C:12]3[CH:17]=[CH:16][C:15]([Cl:18])=[CH:14][C:13]=3[Cl:19])=[N:10][C:6]=2[CH:5]=[CH:4][CH:3]=1.[CH:27](=O)[CH3:28].[C:30](O[BH3-])(=O)[CH3:31].[Na+]>CO.C(O)(=O)C.C(=O)([O-])O.[Na+]>[Cl:19][C:13]1[CH:14]=[C:15]([Cl:18])[CH:16]=[CH:17][C:12]=1[NH:11][C:9]1[N:8]([CH2:20][CH2:21][C:22]([O:24][CH2:25][CH3:26])=[O:23])[C:7]2[C:2]([N:1]([CH2:27][CH3:28])[CH2:30][CH3:31])=[CH:3][CH:4]=[CH:5][C:6]=2[N:10]=1

参加物

7

反応物 3

HCID 177AcetaldehydeHCID 23670382SodiumacetoxyborohydrideHCID 68763200HCID 68763200、化合物

生成物 1

HCID 68761561HCID 68761561、化合物収率 104.2%

試薬・触媒・溶媒 3

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

実験手順

To a solution of ethyl 3-{7-amino-2-[(2,4-dichlorophenyl)amino]-1H-benzimidazol-1-yl}propanoate (Reference Example 27; 214 mg, 0.544 mmol) in methanol (5.5 mL) and acetic acid (0.110 mL) was added acetaldehyde (0.204 mL, 3.27 mmol) at 0° C. The resultant mixture was stirred at 0° C. for 30 min. To the reaction mixture was added sodium acetoxyborohydride (692 mg, 3.27 mmol) at 0° C. After the resultant mixture was stirred at room temperature for 12 hr, the mixture was diluted with aqueous saturated sodium hydrogen carbonate and, extracted with ethyl acetate. The combined organic layer was washed with brine, dried over anhydrous sodium sulfate, filtered and concentrated in vacuo. The residue was purified by column chromatography on NH-silica gel eluting with ethyl acetate to give the title compound as a solid (255 mg, 0.567 mmol, quant).

後処理

  1. extractionextracted with ethyl acetate
  2. washThe combined organic layer was washed with brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by column chromatography on NH-silica gel eluting with ethyl acetate

出典と根拠

ORDレコード
ord-0f4f3821228749febbd17ee8e89b4897
出典データセット
uspto-grants-2014_12
特許番号
US08901141B2

反応ノート

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