Acetic Acid → HCID 67103666, compound

HRID 2080849Notes

Reaction equation

HRID 2080849 reaction equation
[CH3:1][O:2][C:3](=[O:32])[CH2:4][CH2:5][N:6]([CH2:17][C:18]1[CH:23]=[CH:22][C:21]([CH2:24][NH:25][CH2:26][C:27]2[NH:28][CH:29]=[CH:30][N:31]=2)=[CH:20][CH:19]=1)[CH2:7][CH2:8][CH2:9][CH2:10][N:11]1[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]1.[CH3:33][N:34]1[CH:38]=[CH:37][N:36]=[C:35]1[CH:39]=O.C([BH3-])#N.[Na+].C(O)(=O)C>CO>[CH3:1][O:2][C:3](=[O:32])[CH2:4][CH2:5][N:6]([CH2:17][C:18]1[CH:23]=[CH:22][C:21]([CH2:24][N:25]([CH2:26][C:27]2[NH:28][CH:29]=[CH:30][N:31]=2)[CH2:39][C:35]2[N:34]([CH3:33])[CH:38]=[CH:37][N:36]=2)=[CH:20][CH:19]=1)[CH2:7][CH2:8][CH2:9][CH2:10][N:11]1[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16]1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 1395751-Methyl-2-imidazolecarboxaldehydeHCID 5003444Sodium cyanoborohydrideHCID 67103356HCID 67103356, compound

Product 1

HCID 67103666HCID 67103666, compoundYield 68.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

The compound (403 mg) obtained in Example 62-2 was dissolved in anhydrous methanol (16 ml) and added with 1-methyl-2-imidazole carboxaldehyde (151 mg) and sodium cyanoborohydride (172 mg). After the solution was adjusted to pH 5 with acetic acid, the whole was stirred at room temperature for 18 hours. After completion of the reaction, the solvent was distilled off. The resultant was added with a 1 mol/l sodium hydroxide aqueous solution and the whole was subjected to extraction with chloroform. The resultant was dried with magnesium sulfate and the solvent was distilled off. The resultant was purified through silica gel column chromatography (chloroform/ethyl acetate), thereby obtaining the subject compound (333 mg) as a colorless oily substance.

Workup

  1. customAfter completion of the reaction
  2. distillationthe solvent was distilled off
  3. additionThe resultant was added with a 1 mol/l sodium hydroxide aqueous solution
  4. extractionthe whole was subjected to extraction with chloroform
  5. dry with materialThe resultant was dried with magnesium sulfate
  6. distillationthe solvent was distilled off
  7. customThe resultant was purified through silica gel column chromatography (chloroform/ethyl acetate)

Sources & evidence

ORD record
ord-0a90d56d65b945748079b9e59b5915b8
Source dataset
uspto-grants-2011_04
Patent number
US07932281B2

Reaction notes

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