Benzil → 3-(4,5-diphenyl-1H-imidazol-2-yl)propionic acid methyl ester

HRID 220261

Reaction equation

HRID 220261 reaction equation
[C:1]1([C:7]([C:9]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=O)=O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH3:17][O:18][CH:19]([O:26]C)[CH2:20][CH2:21][C:22](OC)=O.C([O-])(=O)C.[NH4+:32].[OH-].[NH4+:34]>C(O)(=O)C.O>[CH3:17][O:18][C:19](=[O:26])[CH2:20][CH2:21][C:22]1[NH:32][C:9]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[C:7]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[N:34]=1

Participants

7

Reactant 4

HCID 8651BenzilHCID 14923Ammonium HydroxideHCID 350846Methyl 4,4-dimethoxybutanoateHCID 517165Ammonium Acetate

Product 1

HCID 684138073-(4,5-diphenyl-1H-imidazol-2-yl)propionic acid methyl ester

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Procedure

A solution of 1 g of benzil, 1.01 g of methyl 4,4-dimethoxybutyrate and 2.87 g of ammonium acetate in 23 mL of acetic acid was refluxed for 5 h. The mixture was poured into water, basified with a 25% aq. ammonium hydroxide solution and extracted with DCM. The organic phase was dried over anh. Na2SO4 and concentrated in vacuo. The resulting crude material was purified by CC using heptane/EtOAc from 85/15 to 0/100 as eluant to yield 633 mg of 3-(4,5-diphenyl-1H-imidazol-2-yl)-propionic acid methyl ester as a yellowish solid.

Workup

  1. extractionextracted with DCM
  2. dry with materialThe organic phase was dried over anh. Na2SO4
  3. concentrationconcentrated in vacuo
  4. customThe resulting crude material was purified by CC

Sources & evidence

ORD record
ord-892bcec21f6c40609c2057332dd0077b
Source dataset
uspto-grants-2012_06
Patent number
US08202885B2

Linked notes

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