Trimethyl orthoformate → HCID 23155396, compound

HRID 2080744Notes

Reaction equation

HRID 2080744 reaction equation
[NH2:1][CH2:2][C:3]1[CH:8]=[CH:7][C:6]([NH:9][C:10]([NH:12][CH2:13][CH2:14][CH2:15][CH2:16][N:17]([CH2:21][CH2:22][CH3:23])[CH2:18][CH2:19][CH3:20])=[O:11])=[C:5](C)[CH:4]=1.[NH:25]1[CH:29]=[CH:28][N:27]=[C:26]1[CH:30]=O.C(OC)(OC)OC.[BH4-].[Na+]>CO>[CH2:21]([N:17]([CH2:18][CH2:19][CH3:20])[CH2:16][CH2:15][CH2:14][CH2:13][NH:12][C:10]([NH:9][C:6]1[CH:5]=[CH:4][C:3]([CH2:2][NH:1][CH2:30][C:26]2[NH:25][CH:29]=[CH:28][N:27]=2)=[CH:8][CH:7]=1)=[O:11])[CH2:22][CH3:23]

Participants

6

Reactant 4

HCID 9005Trimethyl orthoformateHCID 249551H-imidazole-2-carbaldehydeHCID 4311764Sodium borohydrideHCID 67103574HCID 67103574, compound

Product 1

HCID 23155396HCID 23155396, compoundYield 43.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

The compound (195.6 mg) obtained in Example 12-2 was dissolved in anhydrous methanol (7.8 ml) and added with 2-imidazole carboxaldehyde (88.4 mg) and trimethyl orthoformate (0.200 ml) and the whole was stirred at room temperature for 14 hours. Then, the solution was added with sodium borohydride (69.2 mg) and stirred at room temperature for 1.5 hours. After completion of the reaction, the solvent was distilled off under reduced pressure. The resultant was added with water and subjected to extraction with chloroform. The extract was washed with a saturated saline solution and dried with magnesium sulfate. The solvent was distilled off and the residue was purified through silica gel column chromatography (chloroform/methanol), thereby obtaining the subject compound (101 mg) as a colorless oily substance.

Workup

  1. stirringstirred at room temperature for 1.5 hours
  2. customAfter completion of the reaction
  3. distillationthe solvent was distilled off under reduced pressure
  4. additionThe resultant was added with water
  5. extractionsubjected to extraction with chloroform
  6. washThe extract was washed with a saturated saline solution
  7. dry with materialdried with magnesium sulfate
  8. distillationThe solvent was distilled off
  9. customthe residue was purified through silica gel column chromatography (chloroform/methanol)

Sources & evidence

ORD record
ord-ce74d7f2a01c4d4d9b0253dee0cbe5ca
Source dataset
uspto-grants-2011_04
Patent number
US07932281B2

Reaction notes

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