Acetaldehyde → HCID 86632922, 화합물

HRID 1398940노트

반응식

HRID 1398940 반응식
[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

참가 물질

8

반응물 3

HCID 177AcetaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 86632921HCID 86632921, 화합물

생성물 1

HCID 86632922HCID 86632922, 화합물수율 74%

시약·촉매·용매 4

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

실험 절차

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%).

후처리

  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

출처 및 근거

ORD 기록
ord-d7001a52039c4ee8b1c2f7bc3e36a128
출처 데이터셋
uspto-grants-2014_12
특허 번호
US08901141B2

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