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

HRID 466426Notes

Reaction equation

HRID 466426 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) δ 11.31 (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, 3H).

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-b5e04566229846898e68a6b66910be27
Source dataset
uspto-grants-1992_10
Patent number
US05155118

Reaction notes

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