Trimethyl orthoformate → HCID 67103541, compound

HRID 2080871Notes

Reaction equation

HRID 2080871 reaction equation
[CH3:1][O:2][C:3](=[O:26])[CH2:4][N:5]([CH2:17][C:18]1[CH:23]=[CH:22][C:21]([CH2:24][NH2:25])=[CH:20][CH:19]=1)[CH2:6][CH2:7][CH2:8][CH2:9][N:10]([CH2:14][CH2:15][CH3:16])[CH2:11][CH2:12][CH3:13].C(OC)(OC)OC.[C:34]([BH3-])#[N:35].[Na+].[CH3:38][N:39]1[CH:43]=[CH:42][N:41]=[C:40]1[CH:44]=O>CO.C(O)(=O)C>[CH3:1][O:2][C:3](=[O:26])[CH2:4][N:5]([CH2:17][C:18]1[CH:23]=[CH:22][C:21]([CH2:24][N:25]([CH2:7][C:6]2[N:35]([CH3:34])[CH:3]=[CH:4][N:5]=2)[CH2:44][C:40]2[N:39]([CH3:38])[CH:43]=[CH:42][N:41]=2)=[CH:20][CH:19]=1)[CH2:6][CH2:7][CH2:8][CH2:9][N:10]([CH2:14][CH2:15][CH3:16])[CH2:11][CH2:12][CH3:13]

Participants

7

Reactant 4

HCID 9005Trimethyl orthoformateHCID 1395751-Methyl-2-imidazolecarboxaldehyde2×HCID 5003444Sodium cyanoborohydride2×HCID 67103855HCID 67103855, compound

Product 1

HCID 67103541HCID 67103541, compoundYield 87.4%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 887MethanolSolvent3×

Procedure

The compound (1.78 g) obtained in Example 64-1 was dissolved in methanol (30 ml) and added with trimethyl orthoformate (1.8 ml), acetic acid (1.0 ml), and sodium cyanoborohydride (0.324 g). The mixture was gradually added with a methanol solution (5.0 ml) containing 1-methyl-2-imidazole carboxaldehyde (0.550 g) and the whole was stirred at room temperature for 1 hour. Further, sodium cyanoborohydride (0.486 g) and a methanol solution (6.0 ml) containing 1-methyl-2-imidazole carboxaldehyde (0.660 g) were added thereto and the whole was stirred at room temperature for 63 hours. After completion of the reaction, the solvent was distilled off under reduced pressure. The residue was dissolved in chloroform and washed with a saturated aqueous sodium hydrogen carbonate solution and then the whole was subjected to extraction with chloroform. The organic layer was a saturated saline solution and dried with anhydrous sodium sulfate. After filtration, the solvent was distilled off under reduced pressure. The residue was purified through silica gel column chromatography (chloroform/ethyl acetate), thereby obtaining the subject compound (1.18 g) as a colorless oily substance.

Workup

  1. additionwere added
  2. stirringthe whole was stirred at room temperature for 63 hours
  3. customAfter completion of the reaction
  4. distillationthe solvent was distilled off under reduced pressure
  5. dissolutionThe residue was dissolved in chloroform
  6. washwashed with a saturated aqueous sodium hydrogen carbonate solution
  7. extractionthe whole was subjected to extraction with chloroform
  8. dry with materialdried with anhydrous sodium sulfate
  9. filtrationAfter filtration
  10. distillationthe solvent was distilled off under reduced pressure
  11. customThe residue was purified through silica gel column chromatography (chloroform/ethyl acetate)

Sources & evidence

ORD record
ord-61cf445e41fa4e02aa43443e6b7ff477
Source dataset
uspto-grants-2011_04
Patent number
US07932281B2

Reaction notes

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