Ethyl Acetate → Pivaloyloxymethyl 1-[(2'-t-butoxycarbonylbiphenyl-4-yl)methyl]-4-(1-hydroxy-1-methylethyl)-2-propylimidazole-5-carboxylate

HRID 52902Notes

Reaction equation

HRID 52902 reaction equation
[C:1]([O:7][CH2:8]Cl)(=[O:6])[C:2]([CH3:5])([CH3:4])[CH3:3].C(=O)([O-])[O-].[K+].[K+].[C:16]([O:20][C:21]([C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=1[C:29]1[CH:34]=[CH:33][C:32]([CH2:35][N:36]2[C:40]([C:41]([OH:43])=[O:42])=[C:39]([C:44]([OH:47])([CH3:46])[CH3:45])[N:38]=[C:37]2[CH2:48][CH2:49][CH3:50])=[CH:31][CH:30]=1)=[O:22])([CH3:19])([CH3:18])[CH3:17].C(OCC)(=O)C>CN(C)C(=O)C.O>[C:16]([O:20][C:21]([C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=1[C:29]1[CH:34]=[CH:33][C:32]([CH2:35][N:36]2[C:40]([C:41]([O:43][CH2:8][O:7][C:1](=[O:6])[C:2]([CH3:5])([CH3:4])[CH3:3])=[O:42])=[C:39]([C:44]([OH:47])([CH3:46])[CH3:45])[N:38]=[C:37]2[CH2:48][CH2:49][CH3:50])=[CH:31][CH:30]=1)=[O:22])([CH3:19])([CH3:18])[CH3:17]

Participants

7

Reactant 4

HCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 87885Chloromethyl pivalateHCID 106244931-[(2'-t-Butoxycarbonylbiphenyl-4-yl)methyl]-4-(1-hydroxy-1-methylethyl)-2-propylimidazole-5-carboxylic acid

Product 1

HCID 10579348Pivaloyloxymethyl 1-[(2'-t-butoxycarbonylbiphenyl-4-yl)methyl]-4-(1-hydroxy-1-methylethyl)-2-propylimidazole-5-carboxylate

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 31374DimethylacetamideSolvent

Procedure

2.13 ml of chloromethyl pivalate and 3.99 g of potassium carbonate were added to a solution of 6 g of 1-[(2'-t-butoxycarbonylbiphenyl-4-yl)methyl]-4-(1-hydroxy-1-methylethyl)-2-propylimidazole-5-carboxylic acid [prepared as described in step (b) above] in 70 ml of N,N-dimethylacetamide, and the resulting mixture was stirred at room temperature for 1 hour and then at 50° C. for 2 hours. At the end of this time, the reaction mixture was mixed with ethyl acetate and water. The ethyl acetate layer was separated and dried over anhydrous magnesium sulfate, after which the solvent was removed by distillation under reduced pressure. The resulting 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 6.80 g of the title compound as crystals, melting at 106°-107° C.

Workup

  1. waitat 50° C. for 2 hours
  2. customThe ethyl acetate layer was separated
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customafter which the solvent was removed by distillation under reduced pressure
  5. customThe resulting residue was purified by column chromatography through silica gel
  6. additionby volume mixture of ethyl acetate and hexane as the eluent

Sources & evidence

ORD record
ord-ae95c3c6aff84368abaaec0990a628cf
Source dataset
uspto-grants-1997_04
Patent number
US05616599

Reaction notes

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