tert-Butyl 2-bromobutanoate → HCID 66755153, compound

HRID 1632000Notes

Reaction equation

HRID 1632000 reaction equation
[C:1]([O:5][C:6]([N:8]1[C:12]2[CH:13]=[CH:14][C:15]([C:17]#[N:18])=[CH:16][C:11]=2[NH:10][C:9]1=[O:19])=[O:7])([CH3:4])([CH3:3])[CH3:2].[C:20]([O:24][C:25](=[O:30])[CH:26](Br)[CH2:27][CH3:28])([CH3:23])([CH3:22])[CH3:21]>CN(C=O)C.C(OCC)(=O)C>[C:1]([O:5][C:6]([N:8]1[C:12]2[CH:13]=[CH:14][C:15]([C:17]#[N:18])=[CH:16][C:11]=2[N:10]([CH:26]([C:25]([O:24][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:30])[CH2:27][CH3:28])[C:9]1=[O:19])=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 2

HCID 13124118tert-Butyl 2-bromobutanoateHCID 249009585-Cyano-2-oxo-2,3-dihydro-benzoimidazole-1-carboxylic acid tert-butyl ester

Product 1

HCID 66755153HCID 66755153, compoundYield 72.1%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

To a chilled solution of 5-cyano-2-oxo-2,3-dihydro-benzoimidazole-1-carboxylic acid tert-butyl ester (50 mg, 0.19 mmol) in dry DMF (1 mL) NaH (60% dispersion mineral oil, 8 mg, 0.20 mmol) was added under N2 atmosphere. The reaction was stirred at room temperature for 15 min. Then, a solution of tert-butyl-2-bromobutyrate (0.054 mL, 0.29 mmol) in DMF (2 mL) was added at 0° C. The reaction mixture was stirred at room temperature for 3 hours, diluted with ethyl acetate, washed with water, with a saturated NH4Cl aqueous solution, brine, dried over Na2SO4, filtered and concentrated in vacuo. The residue was purified by flash chromatography in silica gel using 15% ethyl acetate in n-heptane as eluent to afford 3-(1-tert-butoxycarbonylpropyl)-5-cyano-2-oxo-2,3-dihydro-benzoimidazole-1-carboxylic acid tert-butyl ester (55 mg, 72%) as a white solid.

Workup

  1. stirringThe reaction mixture was stirred at room temperature for 3 hours
  2. washwashed with water, with a saturated NH4Cl aqueous solution, brine
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by flash chromatography in silica gel using 15% ethyl acetate in n-heptane as eluent

Sources & evidence

ORD record
ord-26d3f138ecb84713b5f39434b46ef75a
Source dataset
uspto-grants-2014_07
Patent number
US08791148B2

Reaction notes

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