HCID 19815285, compound → HCID 19815282, compound

HRID 847043Notes

Reaction equation

HRID 847043 reaction equation
[C:1]([C:5]1[CH:6]=[C:7]([C:11]2[CH:16]=[CH:15][C:14]([CH2:17][N:18]3[C:22]([CH2:23][OH:24])=[C:21](Cl)[N:20]=[C:19]3[CH2:26][CH2:27][CH2:28][CH3:29])=[CH:13][CH:12]=2)[CH:8]=[CH:9][CH:10]=1)([O:3][CH3:4])=[O:2]>CO.[Pd]>[C:1]([C:5]1[CH:6]=[C:7]([C:11]2[CH:16]=[CH:15][C:14]([CH2:17][N:18]3[C:22]([CH2:23][OH:24])=[CH:21][N:20]=[C:19]3[CH2:26][CH2:27][CH2:28][CH3:29])=[CH:13][CH:12]=2)[CH:8]=[CH:9][CH:10]=1)([O:3][CH3:4])=[O:2]

Participants

4

Reactant 1

HCID 19815285HCID 19815285, compound

Product 1

HCID 19815282HCID 19815282, compoundYield 36%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of 1.00 g of 10% palladium/carbon and 1.00 g of 1-[(3'-carbomethoxybiphenyl-4-yl)methyl]-2-butyl-4-chloro-5-hydroxymethyl imidazole in 20 mL of methanol was stirred at 25° for five minutes. Hydrogen gas was bubbled into the solution, and the mixture was stirred under H2 (g) (1 atm.) at 25° for 3.5 hours. The mixture was filtered, and the resulting solution concentrated in vacuo. Column chromatography (elution: 0-5% methanol/chloroform) furnished 0.33 g of 1-[(3'-carbomethoxybiphenyl-4-yl)methyl]-2-butyl-5-hydroxymethyl imidazole. NMR (200 MHz, DMSO-d6) δ8.20 (s, 1H); 7.98 (d, 2H); 7.65 (t, 1H); 7.41 (A2M2, 4H); 6.80 (s, 1H); 5.30 (s, 2H); 5.12 (t, 1H); 4.37 (d, 2H); 3.90 (s, 3H); 2.52 (t, 2H); 1.51 (quint., 2H); 1.27 (sext., 2H); 0.80 (t, 3H).

Workup

  1. customHydrogen gas was bubbled into the solution
  2. stirringthe mixture was stirred under H2 (g) (1 atm.) at 25° for 3.5 hours
  3. filtrationThe mixture was filtered
  4. concentrationthe resulting solution concentrated in vacuo
  5. washColumn chromatography (elution: 0-5% methanol/chloroform)

Sources & evidence

ORD record
ord-e5e85016bdf94cb39bd1f89e7e0f6abf
Source dataset
uspto-grants-1992_08
Patent number
US05138069

Reaction notes

Loading…