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

HRID 2260723노트

반응식

HRID 2260723 반응식
[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]

참가 물질

6

반응물 3

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

생성물 1

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

시약·촉매·용매 2

HCID 23938Palladium촉매HCID 887Methanol용매

반응 조건

온도
50 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-bd7367dff5954afd98f94bebdb299711
출처 데이터셋
uspto-grants-1995_12
특허 번호
US05478858

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