1,1'-Carbonyldiimidazole → 2-Methyl-2-(2-oxo-2,3-dihydro-benzimidazol-1-yl)-propionic acid tert-butyl ester

HRID 1747410Notes

Reaction equation

HRID 1747410 reaction equation
[C:1]([O:5][C:6](=[O:18])[C:7]([NH:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[NH2:17])([CH3:9])[CH3:8])([CH3:4])([CH3:3])[CH3:2].[C:19](N1C=CN=C1)(N1C=CN=C1)=[O:20]>C1COCC1>[C:1]([O:5][C:6](=[O:18])[C:7]([CH3:9])([N:10]1[C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=2[NH:17][C:19]1=[O:20])[CH3:8])([CH3:2])([CH3:3])[CH3:4]

Participants

4

Reactant 2

HCID 682631,1'-CarbonyldiimidazoleHCID 59497586HCID 59497586, compound

Product 1

HCID 594973462-Methyl-2-(2-oxo-2,3-dihydro-benzimidazol-1-yl)-propionic acid tert-butyl esterYield 72.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 2-(2-amino-phenylamino)-2-methyl-propionic acid tert-butyl ester (570 mg, 2.3 mmol) in THF (25 mL) was added 1,1′-carbonyldiimidazole (560 mg, 3.5 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 2-methyl-2-(2-oxo-2,3-dihydro-benzimidazol-1-yl)-propionic acid tert-butyl ester (462 mg, 72%).

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-0ba2b6ffa14d47baa3a4489a5df8d679
Source dataset
uspto-grants-2015_10
Patent number
US09150556B2

Reaction notes

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