HCID 67736190, compound → HCID 22400399, compound

HRID 1757190Notes

Reaction equation

HRID 1757190 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-{(2chlorophenyl)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-a92c2fc3752b45c4b5e8449bd045de8e
Source dataset
uspto-grants-1995_08
Patent number
US05444080

Reaction notes

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