Acetaldehyde → HCID 86632927, 화합물

HRID 1398945노트

반응식

HRID 1398945 반응식
[NH2:1][C:2]1[C:7]2[N:8]([CH2:21][CH2:22][CH2:23][NH:24][C:25](=[O:31])[O:26][C:27]([CH3:30])([CH3:29])[CH3:28])[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:32](=O)[CH3:33].[C:35](O[BH-](OC(=O)C)OC(=O)C)(=O)[CH3:36].[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][CH2:23][NH:24][C:25](=[O:31])[O:26][C:27]([CH3:28])([CH3:30])[CH3:29])[C:7]2[C:2]([N:1]([CH2:32][CH3:33])[CH2:35][CH3:36])=[CH:3][CH:4]=[CH:5][C:6]=2[N:10]=1

참가 물질

8

반응물 3

HCID 177AcetaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 86632926HCID 86632926, 화합물

생성물 1

HCID 86632927HCID 86632927, 화합물수율 90.4%

시약·촉매·용매 4

HCID 176Acetic Acid용매HCID 887Methanol용매HCID 14798Sodium Hydroxide용매HCID 516892Sodium Bicarbonate용매

실험 절차

To a solution of tert-butyl (3-{7-amino-2-[(2,4-dichlorophenyl)(hydroxy)methyl]-1H-benzimidazol-1-yl}propyl)carbamate (3.00 g, 6.45 mmol) in methanol (65 mL) and acetic acid (3.3 mL) was added acetoaldehyde (2.41 mL, 38.7 mmol) at 0° C. The resultant mixture was stirred at 0° C. for 30 min. To the reaction mixture was added sodium triacetoxyborohydride (8.20 g, 38.7 mmol) at 0° C. After the resultant mixture was stirred at 0° C. for 3 h, the mixture was diluted with aqueous sodium hydrogen carbonate and 1N aqueous sodium hydroxide, and extracted with ethyl acetate. The combined organic layer was washed with brine, dried over sodium sulfate, filtered and concentrated in vacuo. The residue was purified by column chromatography on silica gel eluting with a ethyl acetate to give a crude solid, which was washed with diisopropyl ether to give the title compound as a colorless solid (3.04 g, 5.83 mmol, 90%).

후처리

  1. extractionextracted with ethyl acetate
  2. washThe combined organic layer was washed with 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 ethyl acetate
  7. customto give a crude solid, which
  8. washwas washed with diisopropyl ether

출처 및 근거

ORD 기록
ord-8cd5933f096d4c24b6561466228843f4
출처 데이터셋
uspto-grants-2014_12
특허 번호
US08901141B2

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