Dichloromethane → HCID 15698079, compound

HRID 466402Notes

Reaction equation

HRID 466402 reaction equation
C([O:5][C:6]([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[C:14]1[CH:19]=[CH:18][C:17]([CH2:20][N:21]2[C:25]([CH2:26][OH:27])=[C:24]([N+:28]([O-:30])=[O:29])[N:23]=[C:22]2[CH2:31][CH2:32][CH2:33][CH3:34])=[CH:16][CH:15]=1)=[O:7])(C)(C)C.FC(F)(F)C(O)=O.C(Cl)Cl.[OH-].[Na+]>O>[C:6]([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[C:14]1[CH:15]=[CH:16][C:17]([CH2:20][N:21]2[C:25]([CH2:26][OH:27])=[C:24]([N+:28]([O-:30])=[O:29])[N:23]=[C:22]2[CH2:31][CH2:32][CH2:33][CH3:34])=[CH:18][CH:19]=1)([OH:7])=[O:5]

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 6422Trifluoroacetic acidHCID 14798Sodium HydroxideHCID 15698078HCID 15698078, compound

Product 1

HCID 15698079HCID 15698079, compoundYield 85.6%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of 1.98 g of 1[(2'-tert-butoxycarbonylbiphenyl-4-yl)methyl]-2-butyl-5-hydroxymethyl-4-nitroimidazole, 20 mL of trifluoroacetic acid, and 20 mL of methylene chloride was stirred at 25° for 1 hour. At this point, the solution was poured into water. The resulting mixture was adjusted to pH 3 using 10% sodium hydroxide solution and then extracted with chloroform. The combined organic phases were washed with brine, dried over anhydrous magnesium sulfate, filtered, and concentrated in vacuo. Column chromatography (elution: methanol/chloroform) provided 1.49 g of 1-[(2'-carboxybiphenyl-4-yl)methyl]-2-butyl-5-hydroxymethyl-4-nitroimidazole; m.p. 204°-205.5°. NMR (200 MHz, DMSO-d6): δ 7.71 (d, 1H); 7.56 (t, 1H); 7.43 (t, 1H); 7.32 (m, 3H); 7.15 (d, 2H); 5.63 (br s, 1H); 5.42 (s, 2H); 4.83 (s, 2H); 2.54 (t, 2H); 1.50 (quint., 2H); 1.24 (sext., 2H); 0.76 (t, 3H).

Workup

  1. extractionextracted with chloroform
  2. washThe combined organic phases were washed with brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. washColumn chromatography (elution: methanol/chloroform)

Sources & evidence

ORD record
ord-c93ca096fd1445ac90c156051fd61e0c
Source dataset
uspto-grants-1992_10
Patent number
US05155118

Reaction notes

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