Bis-(1H-imidazol-2-YL)-methanone → (S)-3-(2-Oxo-2,3-dihydro-benzoimidazol-1-yl)-hexanoic acid ethyl ester

HRID 1747375Notes

Reaction equation

HRID 1747375 reaction equation
[CH2:1]([O:3][C:4](=[O:18])[CH2:5][C@@H:6]([NH:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[NH2:17])[CH2:7][CH2:8][CH3:9])[CH3:2].[C:19](C1NC=CN=1)(C1NC=CN=1)=[O:20]>C1COCC1>[CH2:1]([O:3][C:4](=[O:18])[CH2:5][C@@H:6]([N:10]1[C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=2[NH:17][C:19]1=[O:20])[CH2:7][CH2:8][CH3:9])[CH3:2]

Participants

4

Reactant 2

HCID 5250894Bis-(1H-imidazol-2-YL)-methanoneHCID 59497425(S)-3-(2-Amino-phenylamino)-hexanoic acid ethyl ester

Product 1

HCID 59497467(S)-3-(2-Oxo-2,3-dihydro-benzoimidazol-1-yl)-hexanoic acid ethyl esterYield 98%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (S)-3-(2-Amino-phenylamino)-hexanoic acid ethyl ester (650 mg, 2.6 mmol) in THF (10 mL) was added carbonyl diimidazole [CDI] (842 mg, 5.2 mmol) at room temperature under nitrogen atmosphere. The solution was stirred at the same temperature for 12 hours. The solution was concentrated and the residue was purified by CombiFlash with 20% EtOAc in Hexane as the eluent to afford the desirable product (S)-3-(2-Oxo-2,3-dihydro-benzoimidazol-1-yl)-hexanoic acid ethyl ester (700 mg, 98%) as a colorless oil.

Workup

  1. concentrationThe solution was concentrated
  2. customthe residue was purified by CombiFlash with 20% EtOAc in Hexane as the eluent

Sources & evidence

ORD record
ord-a6b4107db982477e80ea2f34f50ee4cf
Source dataset
uspto-grants-2015_10
Patent number
US09150556B2

Reaction notes

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