Ethyl Acetate → Methyl 1-[(2'-t-butoxycarbonylbiphenyl-4-yl)methyl]-2-butyl-4-hydroxymethylimidazole-5-carboxylate

HRID 52875Notes

Reaction equation

HRID 52875 reaction equation
[H-].C([Al+]CC(C)C)C(C)C.[C:11]([O:15][C:16]([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=1[C:24]1[CH:29]=[CH:28][C:27]([CH2:30][N:31]2[C:35]([C:36]([O:38][CH3:39])=[O:37])=[C:34]([C:40](OC)=[O:41])[N:33]=[C:32]2[CH2:44][CH2:45][CH2:46][CH3:47])=[CH:26][CH:25]=1)=[O:17])([CH3:14])([CH3:13])[CH3:12].[Cl-].[NH4+].C(OCC)(=O)C>C1(C)C=CC=CC=1.O1CCCC1>[C:11]([O:15][C:16]([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=1[C:24]1[CH:29]=[CH:28][C:27]([CH2:30][N:31]2[C:35]([C:36]([O:38][CH3:39])=[O:37])=[C:34]([CH2:40][OH:41])[N:33]=[C:32]2[CH2:44][CH2:45][CH2:46][CH3:47])=[CH:26][CH:25]=1)=[O:17])([CH3:14])([CH3:13])[CH3:12]

Participants

7

Reactant 4

HCID 8857Ethyl AcetateHCID 25517Ammonium ChlorideHCID 19036225Dimethyl 1-[(2'-t-butoxycarbonylbiphenyl-4-yl)methyl]-2-butylimidazole-4,5-dicarboxylateHCID 21225700Diisobutylaluminumhydride

Product 1

HCID 19036172Methyl 1-[(2'-t-butoxycarbonylbiphenyl-4-yl)methyl]-2-butyl-4-hydroxymethylimidazole-5-carboxylateYield 79.4%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8028TetrahydrofuranSolvent

Procedure

42 ml of diisobutylaluminum hydride (as a 1.5M solution in toluene) were added dropwise at a temperature between -20° C. and -15° C. to a solution of 16.0 g of dimethyl 1-[(2'-t-butoxycarbonylbiphenyl-4yl)methyl]-2-butylimidazole-4,5-dicarboxylate [prepared as described in step (a) above] in 200 ml of tetrahydrofuran, and the resulting mixture was allowed to stand at 0°-5° C. for 16 hours. At the end of this time, the reaction mixture was mixed with an aqueous solution of ammonium chloride and ethyl acetate and was then stirred for 1 hour. After this, precipitates were removed by filtration. The ethyl acetate layer was then separated and dried over anhydrous magnesium sulfate, and the solvent was removed by distillation under reduced pressure. The residue was then purified by column chromatography through silica gel, using ethyl acetate as the eluent, to give 12.0 g of the title compound as crystals, melting at 99° C.

Workup

  1. customAfter this, precipitates
  2. customwere removed by filtration
  3. customThe ethyl acetate layer was then separated
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customthe solvent was removed by distillation under reduced pressure
  6. customThe residue was then purified by column chromatography through silica gel

Sources & evidence

ORD record
ord-ba2a8e04a4414aa19a8e906c43561613
Source dataset
uspto-grants-1997_04
Patent number
US05616599

Reaction notes

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