Sodium hydride → tert-Butyl 2-[4-(2-butyl-4-chloro-5-formyl-imidazol-1-yl-methyl)phenyl]-2-cyclopentylacetate

HRID 1955736Notes

Reaction equation

[H-].[Na+].[CH2:3]([C:7]1[NH:8][C:9]([CH:13]=[O:14])=[C:10]([Cl:12])[N:11]=1)[CH2:4][CH2:5][CH3:6].Br[CH2:16][C:17]1[CH:22]=[CH:21][C:20]([CH:23]([CH:27]2[CH2:31][CH2:30][CH2:29][CH2:28]2)[C:24]([O-:26])=[O:25])=[CH:19][CH:18]=1>CN(C=O)C>[CH2:3]([C:7]1[N:8]([CH2:16][C:17]2[CH:22]=[CH:21][C:20]([CH:23]([CH:27]3[CH2:31][CH2:30][CH2:29][CH2:28]3)[C:24]([O:26][C:17]([CH3:22])([CH3:18])[CH3:16])=[O:25])=[CH:19][CH:18]=2)[C:9]([CH:13]=[O:14])=[C:10]([Cl:12])[N:11]=1)[CH2:4][CH2:5][CH3:6]

Participants

Conditions

Temperature: 0 °C

Procedure

1.6 g (0.053 mol) of sodium hydride (80% strength) are suspended in 50 ml of DMF under protective gas, 10 g (0.053 mol) of 2-butyl-5-formyl-4-chloroimidazole (preparation according to EP 324,377) in 100 ml of DMF are added dropwise at 0° C., the mixture is then stirred at 0° C. for 15 min and 18.9 g (0.053 mol) of tert-butyl 2-(4-bromomethylphenyl-2-cyclopentylacetate in 100 ml of DMF are added dropwise. The mixture is stirred at 0° C. for 2 h, the solvent is evaporated, the residue is taken up in diethyl ether and filtered and, after concentration, chromatographed on silica gel 60 using dichloromethane.

Workup

additionare added dropwise at 0° C.
stirringThe mixture is stirred at 0° C. for 2 h
customthe solvent is evaporated
filtrationfiltered
concentrationafter concentration
customchromatographed on silica gel 60 using dichloromethane

Sources & evidence

ORD record: ord-49c5f9169a18429284a6e12daafcb65e
Source dataset: uspto-grants-1998_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05776964

Reaction notes

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