Ethyl Acetate → HCID 178440080, compound

HRID 265171Notes

Reaction equation

HRID 265171 reaction equation
C(N(CC)C(C)C)(C)C.[OH:10][C:11]([C:14]1[N:15]=[C:16]([CH2:22][CH2:23][CH3:24])[NH:17][C:18]=1[C:19]([OH:21])=[O:20])([CH3:13])[CH3:12].[C:25]([O:31][CH2:32]Cl)(=[O:30])[C:26]([CH3:29])([CH3:28])[CH3:27].C(OCC)(=O)C>CN(C)C(=O)C.O>[OH:10][C:11]([C:14]1[N:15]=[C:16]([CH2:22][CH2:23][CH3:24])[NH:17][C:18]=1[C:19]([O:21][CH2:32][O:31][C:25](=[O:30])[C:26]([CH3:29])([CH3:28])[CH3:27])=[O:20])([CH3:13])[CH3:12]

Participants

7

Reactant 4

HCID 8857Ethyl AcetateHCID 81531DiisopropylethylamineHCID 87885Chloromethyl pivalateHCID 178440085HCID 178440085, compound

Product 1

HCID 178440080HCID 178440080, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 31374DimethylacetamideSolvent

Procedure

1.76 ml of N,N-diisopropylethylamine were added to a suspension of 1.14 g of 4-(1-hydroxy-1-methylethyl)-2-propylimidazole-5-carboxylic acid [prepared as described in step (i) above] in 12 ml of N,N-dimethylacetamide, and the resulting mixture was stirred at room temperature for 10 minutes; 1.36 ml of pivaloyloxymethyl chloride was then added. The reaction mixture was stirred at 60° C. for 4 hours, after which it was mixed with ethyl acetate and water. The ethyl acetate layer was separated and concentrated by evaporation under reduced pressure. The crystals which precipitated were triturated with diisopropyl ether and collected by filtration to give 1.53 g of the title compound, melting at 177° C.

Workup

  1. stirringThe reaction mixture was stirred at 60° C. for 4 hours
  2. customThe ethyl acetate layer was separated
  3. concentrationconcentrated by evaporation under reduced pressure
  4. customThe crystals which precipitated
  5. customwere triturated with diisopropyl ether
  6. filtrationcollected by filtration

Sources & evidence

ORD record
ord-3468c620ca144bc696eed7e98ea626f4
Source dataset
uspto-grants-1997_07
Patent number
US05646171

Reaction notes

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