Acetic Acid → HCID 15698056, compound

HRID 847053Notes

Reaction equation

HRID 847053 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); δ12.75 (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-c68bd00a1b19415e9fd151f0469b2c38
Source dataset
uspto-grants-1992_08
Patent number
US05138069

Reaction notes

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