Acetaldehyde → HCID 68762714, 화합물

HRID 1628578노트

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HRID 1628578 반응식
[NH2:1][C:2]1[C:7]2[N:8]([CH2:21][CH2:22][OH:23])[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:24](=O)[CH3:25].[C:27](O[BH-](OC(=O)C)OC(=O)C)(=O)[CH3:28].[Na+]>CO.C(O)(=O)C.C(=O)([O-])O.[Na+].O>[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][OH:23])[C:7]2[C:2]([N:1]([CH2:24][CH3:25])[CH2:27][CH3:28])=[CH:3][CH:4]=[CH:5][C:6]=2[N:10]=1

참가 물질

8

반응물 3

HCID 177AcetaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 68762744HCID 68762744, 화합물

생성물 1

HCID 68762714HCID 68762714, 화합물수율 99.1%

시약·촉매·용매 4

HCID 176Acetic Acid용매HCID 887Methanol용매HCID 962Water용매HCID 516892Sodium Bicarbonate용매

실험 절차

To a solution of 2-{7-amino-2-[(2,4-dichlorophenyl) (hydroxy)methyl]-1H-benzimidazol-1-yl}ethanol (7.58 g, 21.5 mmol) in methanol (220 mL) and acetic acid (11 mL) was added acetoaldehyde (8.04 mL, 129 mmol) at 0° C. The resultant mixture was stirred at 0° C. for 30 min. To the reaction mixture was added sodium triacetoxyborohydride (27.3 g, 129 mmol) at 0° C. After the resultant mixture was stirred at room temperature for 2 h, the mixture was diluted with aqueous sodium hydrogen carbonate and water, and extracted with ethyl acetate. The combined organic layer was washed with 1N aqueous sodium hydroxide and brine, dried over sodium sulfate, filtered and concentrated in vacuo. The residue was purified by column chromatography on silica gel eluting with ethyl acetate to afford a crude solid, which was washed with diisopropylether to give the title compound as a colorless solid (8.70 g, 21.3 mmol, 99%).

후처리

  1. extractionextracted with ethyl acetate
  2. washThe combined organic layer was washed with 1N aqueous sodium hydroxide 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 ethyl acetate
  7. customto afford a crude solid, which
  8. washwas washed with diisopropylether

출처 및 근거

ORD 기록
ord-173a46d370504371acc4dd2811dd34a3
출처 데이터셋
uspto-grants-2014_07
특허 번호
US08785460B2

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