Acetic Acid → HCID 68772648、化合物

HRID 1398926ノート

反応式

HRID 1398926 の反応式
[NH2:1][C:2]1[C:7]2[N:8]([CH2:21][CH2:22][C:23]([O:25][CH3:26])=[O:24])[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.[C:27](O)(=O)[CH3:28].[CH:31](=O)[CH3:32].C(O[BH3-])(=O)C.[Na+]>CO>[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][C:23]([O:25][CH3:26])=[O:24])[C:7]2[C:2]([N:1]([CH2:27][CH3:28])[CH2:31][CH3:32])=[CH:3][CH:4]=[CH:5][C:6]=2[N:10]=1

参加物

6

反応物 4

HCID 176Acetic AcidHCID 177AcetaldehydeHCID 23670382SodiumacetoxyborohydrideHCID 68773584HCID 68773584、化合物

生成物 1

HCID 68772648HCID 68772648、化合物

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

To a suspension of methyl 3-{7-amino-2-[(2,4-dichlorophenyl)(hydroxy)methyl]-1H-benzimidazol-1-yl}propanoate (6.00 g, 14.7 mmol) and acetic acid (7.4 mL) in methanol (147 mL) was added acetaldehyde (4.95 mL, 88.2 mmol) at 0° C. After 30 min, sodium acetoxyborohydride (18.7 g, 88.2 mmol) was added. After 2 h, the reaction mixture was quenched with water, concentrated in vacuo, diluted with ethyl acetate, washed with aqueous sodium hydroxide (1 M) and brine, dried over sodium sulfate, filtered and concentrated in vacuo. The residue was purified by column chromatography on silica gel eluting with a 10-30% ethyl acetate/n-hexane gradient mixture to give the title compound as a colorless amorphous (6.30 g, 13.6 mmol, 92%).

後処理

  1. waitAfter 2 h
  2. customthe reaction mixture was quenched with water
  3. concentrationconcentrated in vacuo
  4. additiondiluted with ethyl acetate
  5. washwashed with aqueous sodium hydroxide (1 M) and brine
  6. dry with materialdried over sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customThe residue was purified by column chromatography on silica gel eluting with a 10-30% ethyl acetate/n-hexane gradient mixture

出典と根拠

ORDレコード
ord-a6ee35376a1343e29923510a63ddcdb1
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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