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

HRID 1747387Notes

Reaction equation

HRID 1747387 reaction equation
[C:1]([O:5][C:6](=[O:17])[C@@H:7]([NH:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1[NH2:16])[CH3:8])([CH3:4])([CH3:3])[CH3:2].C1N=CN([C:23](N2C=NC=C2)=[O:24])C=1>C1COCC1.C(OCC)(=O)C>[C:1]([O:5][C:6](=[O:17])[C@@H:7]([N:9]1[C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[NH:16][C:23]1=[O:24])[CH3:8])([CH3:2])([CH3:3])[CH3:4]

Participants

5

Reactant 2

HCID 682631,1'-CarbonyldiimidazoleHCID 59497437(S)-2-(2-Amino-phenylamino)-propionic acid tert-butyl ester

Product 1

HCID 59497411(S)-2-(2-Oxo-2,3-dihydro-benzimidazol-1-yl)-propionic acid tert-butyl esterYield 96.8%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of (S)-2-(2-Amino-phenylamino)-propionic acid tert-butyl ester (1.5 g, 6.3 mmol) in THF (10 mL) was added CDI (1.03 g, 6.3 mmol). The reaction mixture was stirred at room temperature for 1 h. When the reaction was completed, the reaction mixture was diluted with ethyl acetate and washed with water. The organic phase was dried over Na2SO4 and concentrated to afford 1.6 g of the desired product as an oily residue. The LCMS indicated only 40% purity; however, this product was used for the next reaction without further purification. LCMS (ESMS): m/z 263.38 (M+H+).

Workup

  1. washwashed with water
  2. dry with materialThe organic phase was dried over Na2SO4
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-289be3a6320b4b1e994da24a42e6e0d3
Source dataset
uspto-grants-2015_10
Patent number
US09150556B2

Reaction notes

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