Sodium Bicarbonate → 1-[(2'-Methoxyaminocarbonylbiphenyl-4-yl)methyl]-2-butyl-4-chloro-5-hydroxymethylimidazole

HRID 847072Notes

Reaction equation

HRID 847072 reaction equation
[CH3:1][O:2][NH:3][C:4]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[C:12]1[CH:17]=[CH:16][C:15]([CH2:18][N:19]2[C:23]([CH2:24][O:25]COCCOC)=[C:22]([Cl:32])[N:21]=[C:20]2[CH2:33][CH2:34][CH2:35][CH3:36])=[CH:14][CH:13]=1)=[O:5].C(=O)(O)[O-].[Na+]>F[B-](F)(F)F.[H+].C(#N)C>[CH3:1][O:2][NH:3][C:4]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[C:12]1[CH:17]=[CH:16][C:15]([CH2:18][N:19]2[C:23]([CH2:24][OH:25])=[C:22]([Cl:32])[N:21]=[C:20]2[CH2:33][CH2:34][CH2:35][CH3:36])=[CH:14][CH:13]=1)=[O:5]

Participants

4

Reactant 2

HCID 516892Sodium BicarbonateHCID 15698090HCID 15698090, compound

Product 1

HCID 156980911-[(2'-Methoxyaminocarbonylbiphenyl-4-yl)methyl]-2-butyl-4-chloro-5-hydroxymethylimidazoleYield 66.3%

Reagents, catalysts & solvents 1

HCID 86745968HCID 86745968, compoundSolvent

Procedure

A solution of 0.20 g of 1-[(2'-methoxyaminocarbonylbiphenyl-4-yl)methyl]-2-butyl-4-chloro-5-(2-methoxyethoxymethoxymethyl)imidazole in 60 ml of 1.5M aqueous tetrafluoroboric acid/acetonitrile was stirred for 20 hours at 25°. The reaction mixture was poured into dilute sodium bicarbonate solution, and the resulting mixture was extracted with diethyl ether. The combined organic phases were washed with brine, dried over anhydrous sodium sulfate, filtered, and concentrated. Column chromatography (elution: methanol/chloroform) provided 0.11 g of 1-[(2'-methoxyaminocarbonylbiphenyl-4-yl)methyl]-2-butyl-4-chloro-5-hydroxymethylimidazole. NMR (200 MHz, CDCl3) δ11.31 (br s, 1H); 7.48 (m, 1H); 7.41-7.33 (m, 5H); 7.09 (d, 2H); 5.27 (br s, 3H); 4.32 (d, 2H); 3.44 (s, 3H); 2.49 (t, 2H); 1.48 (quint., 2H); 1.25 (sext., 2H); 0.80 (t, 3 H).

Workup

  1. extractionthe resulting mixture was extracted with diethyl ether
  2. washThe combined organic phases were washed with brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. washColumn chromatography (elution: methanol/chloroform)

Sources & evidence

ORD record
ord-6359bcad72104275b3ccdf9b363898a3
Source dataset
uspto-grants-1992_08
Patent number
US05138069

Reaction notes

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