Acetic Acid → HCID 68767160, compound

HRID 1173955Notes

Reaction equation

HRID 1173955 reaction equation
[C:1]([O:5][C:6](=[O:30])[NH:7][CH2:8][CH2:9][CH2:10][CH2:11][NH:12][S:13]([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)(=[O:15])=[O:14])([CH3:4])([CH3:3])[CH3:2].[CH3:31][N:32]1[CH:36]=[CH:35][N:34]=[C:33]1[CH:37]=O.C([BH3-])#N.[Na+].C(O)(=O)C>CO>[C:1]([O:5][C:6](=[O:30])[NH:7][CH2:8][CH2:9][CH2:10][CH2:11][NH:12][S:13]([C:16]1[CH:17]=[CH:18][C:19]([CH2:22][N:23]([CH2:24][C:25]2[NH:26][CH:27]=[CH:28][N:29]=2)[CH2:37][C:33]2[N:32]([CH3:31])[CH:36]=[CH:35][N:34]=2)=[CH:20][CH:21]=1)(=[O:14])=[O:15])([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 1395751-Methyl-2-imidazolecarboxaldehydeHCID 5003444Sodium cyanoborohydrideHCID 66941422HCID 66941422, compound

Product 1

HCID 68767160HCID 68767160, compoundYield 91.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

The compound (817.3 mg) obtained in Example 102-2 was dissolved in anhydrous methanol (24.5 ml) and added with 1-methyl-2-imidazolealdehyde (309.4 mg) and sodium cyanoborohydride (235.0 mg). Then, the solution was adjusted to pH 5 with acetic acid and stirred at room temperature for 24 hours. After the reaction, the solvent was distilled off. The residue was added with a 1 mol/l sodium hydroxide aqueous solution and then subjected to extraction with chloroform. The extract was dried with anhydrous magnesium sulfate and the solvent was distilled off. Subsequently, the residue was purified through silica gel column chromatography (chloroform/methanol), thereby obtaining the subject compound (910.0 mg) as a white solid.

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. customSubsequently, the residue was purified through silica gel column chromatography (chloroform/methanol)

Sources & evidence

ORD record
ord-0a2f72b688594bc0ba2b0913fecad592
Source dataset
uspto-grants-2010_11
Patent number
US07833991B2

Reaction notes

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