Acetic Acid → HCID 15698056, compound

HRID 466406Notes

Reaction equation

HRID 466406 reaction equation
[C:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[C:10]1[CH:15]=[CH:14][C:13]([CH2:16][N:17]2[C:21]([CH:22]=[O:23])=[C:20]([Cl:24])[N:19]=[C:18]2[CH2:25][CH2:26][CH2:27][CH3:28])=[CH:12][CH:11]=1)([OH:3])=[O:2].[C-]#N.[Na+].[C:32](O)(=[O:34])C>CO.[O-2].[O-2].[Mn+4]>[C:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[C:10]1[CH:11]=[CH:12][C:13]([CH2:16][N:17]2[C:21]([C:22]([O:34][CH3:32])=[O:23])=[C:20]([Cl:24])[N:19]=[C:18]2[CH2:25][CH2:26][CH2:27][CH3:28])=[CH:14][CH:15]=1)([OH:3])=[O:2]

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 8929Sodium CyanideHCID 11625408HCID 11625408, compound

Product 1

HCID 15698056HCID 15698056, compound

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 887MethanolSolvent

Conditions

Temperature
25 °C

Procedure

To a mixture of 1.45 g of 1-[(2'-carboxybiphenyl-4-yl)methyl]-2-butyl-4-chloroimidazole-5-carboxaldehyde and 0.91 g of sodium cyanide in 20 mL of methanol at 25° C. was added 0.32 mL of acetic acid followed by 7.25 g of manganese dioxide. The resulting mixture was stirred at 25° C. for 40 hours. The reaction mixture was filtered through Celite®, and the filtrate diluted with water. The aqueous solution was adjusted to pH 3 using hydrochloric acid and extracted with methylene chloride. The combined organic phases were washed with brine, dried over anhydrous sodium sulfate, filtered, and concentrated. The crude product was recrystallized from diethyl ether to afford 0.90 g of methyl 1-[(2'-carboxybiphenyl-4-yl)methyl]-2-butyl-4-chloroimidazole-5-carboxylate (m.p. 154°-155° C.). NMR (200 MHz, DMSO-d6); δ 12.75 (br s, 1H), 7.73 (d, 1H) 7.58 (t, 1H), 7.46 (t, 1H), 7.34 (m, 3H), 7.07 (d, 2H), 5.63 (s, 2H), 3.78 (s, 3H), 2.67 (t, 2H), 1.56 (quint., 2H), 1.29 (sext., 2H), 0.83 (t, 3H).

Workup

  1. filtrationThe reaction mixture was filtered through Celite®
  2. additionthe filtrate diluted with water
  3. extractionextracted with methylene chloride
  4. washThe combined organic phases were washed with brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe crude product was recrystallized from diethyl ether

Sources & evidence

ORD record
ord-d9fbe23c81e144128380da635bb2e46b
Source dataset
uspto-grants-1992_10
Patent number
US05155118

Reaction notes

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