1,1'-Carbonyldiimidazole → 4-(2-Oxo-2,3-dihydro-benzimidazol-1-yl)-pentanoic acid methyl ester

HRID 1747396Notes

Reaction equation

HRID 1747396 reaction equation
[CH3:1][O:2][C:3](=[O:16])[CH2:4][CH2:5][CH:6]([NH:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[NH2:15])[CH3:7].[C:17](N1C=CN=C1)(N1C=CN=C1)=[O:18]>C1COCC1>[CH3:1][O:2][C:3](=[O:16])[CH2:4][CH2:5][CH:6]([N:8]1[C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[NH:15][C:17]1=[O:18])[CH3:7]

Participants

4

Reactant 2

HCID 682631,1'-CarbonyldiimidazoleHCID 59497642HCID 59497642, compound

Product 1

HCID 594972784-(2-Oxo-2,3-dihydro-benzimidazol-1-yl)-pentanoic acid methyl esterYield 94.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 4-(2-amino-phenylamino)-pentanoic acid methyl ester (1.05 g, 4.7 mmol) in THF (15 mL) was added 1,1′-carbonyldiimidazole (0.8 g, 4.9 mmol). The solution was stirred at room temperature for 16 hours. The reaction mixture was concentrated. The resulting residue was purified by CombiFlash with 50% EtOAc in Hexane as the eluent to afford the desired 4-(2-oxo-2,3-dihydro-benzimidazol-1-yl)-pentanoic acid methyl ester (1.1 g, 94%).

Workup

  1. concentrationThe reaction mixture was concentrated
  2. customThe resulting residue was purified by CombiFlash with 50% EtOAc in Hexane as the eluent

Sources & evidence

ORD record
ord-8fbf14ba964f44e8ad0ba419f068c57f
Source dataset
uspto-grants-2015_10
Patent number
US09150556B2

Reaction notes

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