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

HRID 265025Notes

Reaction equation

HRID 265025 reaction equation
C(=O)([O-])[O-].[K+].[K+].[C:7]([O: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]([OH:34])=[O:33])=[C:30]([CH2:35][OH:36])[N:29]=[C:28]2[CH2:37][CH2:38][CH2:39][CH3:40])=[CH:22][CH:21]=1)=[O:13])([CH3:10])([CH3:9])[CH3:8].[C:41]([O:47][CH2:48]Cl)(=[O:46])[C:42]([CH3:45])([CH3:44])[CH3:43].C(OCC)(=O)C>CN(C)C(=O)C.O>[C:7]([O: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][CH2:48][O:47][C:41](=[O:46])[C:42]([CH3:45])([CH3:44])[CH3:43])=[O:33])=[C:30]([CH2:35][OH:36])[N:29]=[C:28]2[CH2:37][CH2:38][CH2:39][CH3:40])=[CH:22][CH:21]=1)=[O:13])([CH3:10])([CH3:9])[CH3:8]

Participants

7

Reactant 4

HCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 87885Chloromethyl pivalateHCID 190361191-[(2'-t-Butoxycarbonylbiphenyl-4-yl)methyl]-2-butyl-4-hydroxymethylimidazole-5-carboxylic acid

Product 1

HCID 19036181Pivaloyloxymethyl 1-[(2'-t-butoxycarbonylbiphenyl-4-yl)methyl]-2-butyl-4-hydroxymethylimidazole-5-carboxylateYield 90.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 31374DimethylacetamideSolvent

Procedure

350 mg of potassium carbonate were added to a solution of 552 mg of 1-[(2'-t-butoxycarbonylbiphenyl-4-yl)methyl]-2-butyl-4-hydroxymethylimidazole-5-carboxylic acid (prepared as described in Example 4) and 220 mg of pivaloyloxymethyl chloride in 7 ml of N,N-dimethylacetamide, and the resulting mixture was stirred at room temperature for 5 hours. At the end of this time, the reaction mixture was mixed with ethyl acetate and water, and the ethyl acetate layer was separated and dried over anhydrous magnesium sulfate; the solvent was then removed by distillation under reduced pressure. The resulting residue was purified by column chromatography through silica gel, using ethyl acetate as the eluent, to give 0.62 g of the title compound as a syrup.

Workup

  1. customthe ethyl acetate layer was separated
  2. dry with materialdried over anhydrous magnesium sulfate
  3. customthe solvent was then removed by distillation under reduced pressure
  4. customThe resulting residue was purified by column chromatography through silica gel

Sources & evidence

ORD record
ord-1d7d6f39ca904765837d847d203b7523
Source dataset
uspto-grants-1997_07
Patent number
US05646171

Reaction notes

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