HCID 66755153, compound → HCID 66754697, compound

HRID 1632001Notes

Reaction equation

HRID 1632001 reaction equation
C(OC([N:8]1[C:12]2[CH:13]=[CH:14][C:15]([C:17]#[N:18])=[CH:16][C:11]=2[N:10]([CH:19]([C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[CH2:20][CH3:21])[C:9]1=[O:29])=O)(C)(C)C>C(Cl)Cl>[C:25]([O:24][C:22](=[O:23])[CH:19]([N:10]1[C:11]2[CH:16]=[C:15]([C:17]#[N:18])[CH:14]=[CH:13][C:12]=2[NH:8][C:9]1=[O:29])[CH2:20][CH3:21])([CH3:26])([CH3:27])[CH3:28]

Participants

3

Reactant 1

HCID 66755153HCID 66755153, compound

Product 1

HCID 66754697HCID 66754697, compoundYield 68%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 3-(1-tert-butoxycarbonyl-propyl)-5-cyano-2-oxo-2,3-dihydrobenzoimidazole-1-carboxylic acid tert-butyl ester (55 mg, 0.14 mmol) in CH2Cl2 (5 mL) trifluoroacetic acid (0.10 mL) was added. The reaction mixture was stirred at room temperature for 4 hours, concentrated in vacuo and co-evaporated the solvent with toluene (3×). The residue was purified by flash chromatography in silica gel using 40% ethyl acetate in n-heptane as eluent to afford 2-(6-cyano-2-oxo-2,3-dihydro-benzoimidazol-1-yl)-butyric acid tert-butyl ester (28 mg, 68%) as a white solid.

Workup

  1. concentrationconcentrated in vacuo
  2. customThe residue was purified by flash chromatography in silica gel using 40% ethyl acetate in n-heptane as eluent

Sources & evidence

ORD record
ord-7d665509a8bc4c4c960fe472dc50692c
Source dataset
uspto-grants-2014_07
Patent number
US08791148B2

Reaction notes

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