HCID 67736190, compound → HCID 22400399, compound

HRID 260747Notes

Reaction equation

HRID 260747 reaction equation
Cl.[CH2:2]([C:6]1[N:7]([CH2:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=2[Cl:27])[C:8]([CH:11]=[C:12]([CH2:16][CH2:17][CH2:18][CH3:19])[C:13]([OH:15])=[O:14])=[CH:9][N:10]=1)[CH2:3][CH2:4][CH3:5].[CH2:28]([Li])CCC>CO.[Pt]=O>[ClH:27].[CH2:2]([C:6]1[N:7]([CH2:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=2[Cl:27])[C:8]([CH2:11][CH:12]([CH2:16][CH2:17][CH2:18][CH3:19])[C:13]([O:15][CH3:28])=[O:14])=[CH:9][N:10]=1)[CH2:3][CH2:4][CH3:5]

Participants

5

Reactant 2

HCID 67736190HCID 67736190, compoundHCID 178418339Butyllithium

Product 1

HCID 22400399HCID 22400399, compoundYield 74%

Reagents, catalysts & solvents 2

HCID 82844Platinum oxide (PtO)CatalystHCID 887MethanolSolvent

Procedure

A mixture of methyl (E and Z)-3-[2-n-butyl-1-{(2-chlorophenyl)methyl}-1H-imidazol-5-yl]-2-n-butyl-propenoate hydrochloride salt (prepared by the method in Example 6, replacing methyl lithium with butyl lithium) (245 mg, 0.578 mmol) in methanol (15 mL) and platinum oxide (30 mg) was stirred under an atmosphere of hydrogen for 0.5 hours. The catalyst was filtered, the filtrate was concentrated, and the residue was triturated with diethyl ether to afford 181 mg (74%) of methyl 3-[2-n-butyl-1-{(2-chlorophenyl)methyl}-1H-imidazol-5-yl]-2-n-butylpropanoate hydrochloride; mp 123°-125° C.

Workup

  1. customprepared by the method in Example 6
  2. filtrationThe catalyst was filtered
  3. concentrationthe filtrate was concentrated
  4. customthe residue was triturated with diethyl ether

Sources & evidence

ORD record
ord-ab1a1b05f91f40ddaeac04d15d51e6cb
Source dataset
uspto-grants-1996_06
Patent number
US05530017

Reaction notes

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