Ethyl Acetate → 5-Amino-1-1-butoxycarbonyl-4-methylbenzimidazole

HRID 2260723ノート

反応式

HRID 2260723 の反応式
[C:1]([O:5][C:6]([N:8]1[C:12]2[CH:13]=[CH:14][C:15]([N+:18]([O-])=O)=[C:16]([CH3:17])[C:11]=2[N:10]=[CH:9]1)=[O:7])([CH3:4])(C)C.[C:21](OCC)(=O)[CH3:22].C([O-])=O.[NH4+]>CO.[Pd]>[NH2:18][C:15]1[CH:14]=[CH:13][C:12]2[N:8]([C:6]([O:5][CH2:1][CH2:4][CH2:21][CH3:22])=[O:7])[CH:9]=[N:10][C:11]=2[C:16]=1[CH3:17]

参加物

6

反応物 3

HCID 8857Ethyl AcetateHCID 2723923Ammonium formateHCID 158963171h-Benzimidazole-1-carboxylic acid,4-methyl-5-nitro-,1,1-dimethylethyl ester

生成物 1

HCID 677887485-Amino-1-1-butoxycarbonyl-4-methylbenzimidazole

試薬・触媒・溶媒 2

HCID 23938Palladium触媒HCID 887Methanol溶媒

反応条件

温度
50 °C

実験手順

To a solution of 1-tert-butoxycarbonyl-4-methyl-5-nitrobenzimidazole (8 g) in methanol (40 mL)/ethyl acetate (400 mL) is added palladium-on-carbon (Pd/C) (10%, 0.5 g) and ammonium formate (7.27g). The mixture is stirred at 50° C. for 2 hours, then filtered on Celite, with methanol wash of the solids. The filtrate is rotary evaporated and the residue partitioned between water and ethyl acetate. The organic layer is washed with saturated ammonium chloride, dried over magnesium sulfate, filtered and rotary evaporated to afford pure 5-amino-1-1-butoxycarbonyl-4-methylbenzimidazole as an off-white solid.

後処理

  1. filtrationfiltered on Celite, with methanol
  2. washwash of the solids
  3. customThe filtrate is rotary evaporated
  4. customthe residue partitioned between water and ethyl acetate
  5. washThe organic layer is washed with saturated ammonium chloride
  6. dry with materialdried over magnesium sulfate
  7. filtrationfiltered
  8. customrotary evaporated

出典と根拠

ORDレコード
ord-bd7367dff5954afd98f94bebdb299711
出典データセット
uspto-grants-1995_12
特許番号
US05478858

反応ノート

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