Oxalyl chloride → Ethyl 1-((2'-cyano(1,1'-biphenyl)-4-yl)methyl)-4-(1-hydroxy-1-methylethyl)-2-propyl-1H-imidazole-5-carboxylate

HRID 52965Notes

Reaction equation

HRID 52965 reaction equation
C(Cl)(=O)C(Cl)=O.C([NH:11][C:12]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[C:20]1[CH:25]=[CH:24][C:23]([CH2:26][N:27]2[C:31]([C:32]([O:34][CH2:35][CH3:36])=[O:33])=[C:30]([C:37]([OH:40])([CH3:39])[CH3:38])[N:29]=[C:28]2[CH2:41][CH2:42][CH3:43])=[CH:22][CH:21]=1)=O)(C)(C)C>C(Cl)Cl.C(=O)([O-])O.[Na+].C(OCC)(=O)C>[C:12]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[C:20]1[CH:25]=[CH:24][C:23]([CH2:26][N:27]2[C:31]([C:32]([O:34][CH2:35][CH3:36])=[O:33])=[C:30]([C:37]([OH:40])([CH3:38])[CH3:39])[N:29]=[C:28]2[CH2:41][CH2:42][CH3:43])=[CH:22][CH:21]=1)#[N:11]

Participants

6

Reactant 2

HCID 65578Oxalyl chlorideHCID 19036152Ethyl 1-{4-[2-(t-butylaminocarbonyl)phenyl]phenyl}methyl-4-(1-hydroxy-1-methylethyl)-2-propylimidazole-5-carboxylate

Product 1

HCID 15461993Ethyl 1-((2'-cyano(1,1'-biphenyl)-4-yl)methyl)-4-(1-hydroxy-1-methylethyl)-2-propyl-1H-imidazole-5-carboxylateYield 80.9%

Reagents, catalysts & solvents 3

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolventHCID 516892Sodium BicarbonateSolvent

Procedure

0.345 ml of oxalyl chloride was added dropwise, whilst ice-cooling, to a solution of 1.00 g of ethyl 1-{4-[2-(t-butylaminocarbonyl)phenyl]phenyl}methyl-4-(1-hydroxy-1-methylethyl)-2-propylimidazole-5-carboxylate [prepared as described in step (a) above] in 10 ml of methylene chloride, and the mixture was stirred at the same temperature for 2 hours. At the end of this time, the reaction mixture was diluted with an aqueous solution of sodium hydrogencarbonate and ethyl acetate, and the ethyl acetate layer was separated, dried over anhydrous magnesium sulfate and concentrated by evaporation under reduced pressure. The residue was purified by column chromatography through silica gel, using a 1:1 by volume mixture of ethyl acetate and hexane as the eluent, to give 0.69 g of the title compound as crystals.

Workup

  1. customthe ethyl acetate layer was separated
  2. dry with materialdried over anhydrous magnesium sulfate
  3. concentrationconcentrated by evaporation under reduced pressure
  4. customThe residue was purified by column chromatography through silica gel
  5. additionby volume mixture of ethyl acetate and hexane as the eluent

Sources & evidence

ORD record
ord-c26bfc275e1c48588343a28324306729
Source dataset
uspto-grants-1997_04
Patent number
US05616599

Reaction notes

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