1,1'-Carbonyldiimidazole → (S)-3-(6-Methyl-2-oxo-2,3-dihydro-benzimidazol-1-yl)-5-phenyl-pentanoic acid ethyl ester

HRID 1747294Notes

Reaction equation

HRID 1747294 reaction equation
[CH2:1]([O:3][C:4](=[O:24])[CH2:5][C@@H:6]([NH:15][C:16]1[CH:21]=[C:20]([CH3:22])[CH:19]=[CH:18][C:17]=1[NH2:23])[CH2:7][CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)[CH3:2].C1N=CN([C:30](N2C=NC=C2)=[O:31])C=1>C1COCC1.C(Cl)Cl>[CH2:1]([O:3][C:4](=[O:24])[CH2:5][C@@H:6]([N:15]1[C:16]2[CH:21]=[C:20]([CH3:22])[CH:19]=[CH:18][C:17]=2[NH:23][C:30]1=[O:31])[CH2:7][CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)[CH3:2]

Participants

5

Reactant 2

HCID 682631,1'-CarbonyldiimidazoleHCID 59497376(S)-3-(2-Amino-5-methyl-phenylamino)-5-phenyl-pentanoic acid ethyl ester

Product 1

HCID 59497622(S)-3-(6-Methyl-2-oxo-2,3-dihydro-benzimidazol-1-yl)-5-phenyl-pentanoic acid ethyl esterYield 81.9%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (S)-3-(2-Amino-5-methyl-phenylamino)-5-phenyl-pentanoic acid ethyl ester (0.84 g, 2.6 mmol) in THF (15 mL) was added CDI (0.50 g, 3.1 mmol). The reaction mixture was stirred at room temperature for 16 h. When the reaction was complete, the reaction mixture was diluted with CH2Cl2 and washed with water. The organic phase was dried over Na2SO4 and concentrated to afford 0.75 g of the desired product as a dark brown solid. The resulting residue was used for the next reaction without further purification.

Workup

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

Sources & evidence

ORD record
ord-85f5c24674654dd099d58afcf12174a8
Source dataset
uspto-grants-2015_10
Patent number
US09150556B2

Reaction notes

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