Acetic Acid → HCID 11677629, compound

HRID 2080787Notes

Reaction equation

HRID 2080787 reaction equation
[CH2:1]([N:3]([CH2:15][C:16]1[CH:21]=[CH:20][C:19]([CH2:22][NH:23][CH2:24][C:25]2[NH:26][CH:27]=[CH:28][N:29]=2)=[CH:18][CH:17]=1)[CH2:4][CH2:5][CH2:6][CH2:7][N:8]([CH2:12][CH2:13][CH3:14])[CH2:9][CH2:10][CH3:11])[CH3:2].C([BH3-])#N.[Na+].C(O)(=O)C.[CH3:38][N:39]1[CH:43]=[CH:42][N:41]=[C:40]1[CH:44]=O>CO>[CH2:1]([N:3]([CH2:15][C:16]1[CH:21]=[CH:20][C:19]([CH2:22][N:23]([CH2:24][C:25]2[NH:29][CH:28]=[CH:27][N:26]=2)[CH2:44][C:40]2[N:39]([CH3:38])[CH:43]=[CH:42][N:41]=2)=[CH:18][CH:17]=1)[CH2:4][CH2:5][CH2:6][CH2:7][N:8]([CH2:9][CH2:10][CH3:11])[CH2:12][CH2:13][CH3:14])[CH3:2]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 1395751-Methyl-2-imidazolecarboxaldehydeHCID 5003444Sodium cyanoborohydrideHCID 23155374HCID 23155374, compound

Product 1

HCID 11677629HCID 11677629, compoundYield 81.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

The compound (317 mg) obtained in Example 23-7 was dissolved in anhydrous methanol (6.0 ml) and added with sodium cyanoborohydride (74.8 mg), acetic acid (1.00 ml), and 1-methyl-2-imidazole carboxaldehyde (105 mg) and the whole was stirred overnight at room temperature under a nitrogen atmosphere. After completion of the reaction, the solvent was distilled off and the resultant was dissolved in chloroform and added with a 1 mol/l sodium hydroxide aqueous solution. The whole was stirred for a while and subjected to extraction with chloroform, followed by washing with a saturated aqueous sodium hydrogen carbonate solution and a saturated saline solution. The organic layer obtained was dried with anhydrous sodium sulfate. The solvent was distilled off. The residue was purified through silica gel column chromatography (chloroform/ethyl acetate) and treated with hydrochloric acid, thereby obtaining a hydrochloride (318 mg) of the subject compound as a white solid.

Workup

  1. customAfter completion of the reaction
  2. distillationthe solvent was distilled off
  3. dissolutionthe resultant was dissolved in chloroform
  4. additionadded with a 1 mol/l sodium hydroxide aqueous solution
  5. stirringThe whole was stirred for a while
  6. extractionsubjected to extraction with chloroform
  7. washby washing with a saturated aqueous sodium hydrogen carbonate solution
  8. customThe organic layer obtained
  9. dry with materialwas dried with anhydrous sodium sulfate
  10. distillationThe solvent was distilled off
  11. customThe residue was purified through silica gel column chromatography (chloroform/ethyl acetate)
  12. additiontreated with hydrochloric acid

Sources & evidence

ORD record
ord-4eb0ebd69910445696707dc9978dead3
Source dataset
uspto-grants-2011_04
Patent number
US07932281B2

Reaction notes

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