[3-(2-Amino-3-nitro-phenylcarbamoyl)-propyl]methyl-carbamic acid tert-butyl ester → methyl-[3-(4-nitro-1H-benzoimidazol-2-yl)-propyl]-carbamic acid tert-butyl ester

HRID 220281

Reaction equation

HRID 220281 reaction equation
[C:1]([O:5][C:6](=[O:25])[N:7]([CH2:9][CH2:10][CH2:11][C:12](=O)[NH:13][C:14]1[CH:19]=[CH:18][CH:17]=[C:16]([N+:20]([O-:22])=[O:21])[C:15]=1[NH2:23])[CH3:8])([CH3:4])([CH3:3])[CH3:2]>C(O)(=O)C>[C:1]([O:5][C:6](=[O:25])[N:7]([CH3:8])[CH2:9][CH2:10][CH2:11][C:12]1[NH:13][C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([N+:20]([O-:22])=[O:21])[C:15]=2[N:23]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

3

Reactant 1

HCID 68412474[3-(2-Amino-3-nitro-phenylcarbamoyl)-propyl]methyl-carbamic acid tert-butyl ester

Product 1

HCID 68412537methyl-[3-(4-nitro-1H-benzoimidazol-2-yl)-propyl]-carbamic acid tert-butyl esterYield 91%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A solution of 4.4 g of [3-(2-amino-3-nitro-phenylcarbamoyl)-propyl]methyl-carbamic acid tert-butyl ester in 36 mL of acetic acid was heated at 90° C. for 5 h and concentrated in vacuo. The residue was taken up in DCM, washed with sat. NaHCO3 solution, dried over anh. Na2SO4 and concentrated in vacuo to yield 3.8 g of methyl-[3-(4-nitro-1H-benzoimidazol-2-yl)-propyl]-carbamic acid tert-butyl ester as dark yellow oil.

Workup

  1. concentrationconcentrated in vacuo
  2. washwashed with sat. NaHCO3 solution
  3. dry with materialdried over anh. Na2SO4
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-4aded8f57dda4ab0a40aa39f5dd8194c
Source dataset
uspto-grants-2012_06
Patent number
US08202885B2

Linked notes

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