Acetic Acid → HCID 66941909, compound

HRID 348708Notes

Reaction equation

HRID 348708 reaction equation
[CH2:1]([O:8][C:9](=[O:32])[NH:10][CH2:11][CH2:12][CH2:13][CH2:14][N:15]([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)[CH3:16])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=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>[CH2:1]([O:8][C:9](=[O:32])[NH:10][CH2:11][CH2:12][CH2:13][CH2:14][N:15]([CH2:17][C:18]1[CH:19]=[CH:20][C:21]([CH2:24][N:25]([CH2:26][C:27]2[NH:31][CH:30]=[CH:29][N:28]=2)[CH2:39][C:35]2[N:34]([CH3:33])[CH:38]=[CH:37][N:36]=2)=[CH:22][CH:23]=1)[CH3:16])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 1395751-Methyl-2-imidazolecarboxaldehydeHCID 5003444Sodium cyanoborohydrideHCID 66941783HCID 66941783, compound

Product 1

HCID 66941909HCID 66941909, compoundYield 67.9%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

The compound (608.7 mg) obtained in Example 103-5 was dissolved in anhydrous methanol (24 ml) and added with 1-methyl-2-imidazole carboxaldehyde (231.3 mg) and sodium cyanoborohydride (176.0 mg). The solution was adjusted to pH 5 with acetic acid, followed by stirring at room temperature for 3 days. After the reaction, the solvent was distilled off. The residue was added with a 1 mol/l sodium hydroxide aqueous solution and subjected to extraction with chloroform. The extract was dried with anhydrous magnesium sulfate. The solvent was distilled off and the residue was then purified through silica gel column chromatography (chloroform/methanol), thereby obtaining the subject compound (502.6 mg) as a colorless oily substance.

Workup

  1. customAfter the reaction
  2. distillationthe solvent was distilled off
  3. additionThe residue was added with a 1 mol/l sodium hydroxide aqueous solution
  4. extractionsubjected to extraction with chloroform
  5. dry with materialThe extract was dried with anhydrous magnesium sulfate
  6. distillationThe solvent was distilled off
  7. customthe residue was then purified through silica gel column chromatography (chloroform/methanol)

Sources & evidence

ORD record
ord-fab86d1282bd4b8fa75d8263153d456c
Source dataset
uspto-grants-2007_02
Patent number
US07176227B2

Reaction notes

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