Trimethyl orthoformate → HCID 23155374, compound

HRID 2080786Notes

Reaction equation

HRID 2080786 reaction equation
[NH2:1][CH2:2][C:3]1[CH:23]=[CH:22][C:6]([CH2:7][N:8]([CH2:20][CH3:21])[CH2:9][CH2:10][CH2:11][CH2:12][N:13]([CH2:17][CH2:18][CH3:19])[CH2:14][CH2:15][CH3:16])=[CH:5][CH:4]=1.C(OC)(OC)OC.[NH:31]1[CH:35]=[CH:34][N:33]=[C:32]1[CH:36]=O.[BH4-].[Na+]>CO>[CH2:20]([N:8]([CH2:7][C:6]1[CH:22]=[CH:23][C:3]([CH2:2][NH:1][CH2:36][C:32]2[NH:31][CH:35]=[CH:34][N:33]=2)=[CH:4][CH:5]=1)[CH2:9][CH2:10][CH2:11][CH2:12][N:13]([CH2:17][CH2:18][CH3:19])[CH2:14][CH2:15][CH3:16])[CH3:21]

Participants

6

Reactant 4

HCID 9005Trimethyl orthoformateHCID 249551H-imidazole-2-carbaldehydeHCID 4311764Sodium borohydrideHCID 23155592HCID 23155592, compound

Product 1

HCID 23155374HCID 23155374, compoundYield 115.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

The compound (219 mg) obtained in Example 23-6 was dissolved in anhydrous methanol (5.0 ml) and added with trimethyl orthoformate (112 μl) and 2-imidazole carboxaldehyde (72.4 mg) and the whole was stirred overnight at room temperature, under a nitrogen atmosphere. Subsequently, sodium borohydride (12.3 mg) was added thereto in an ice bath, and the whole was stirred at room temperature for 1 hour. After completion of the reaction, distilled water was added thereto and the whole was stirred for a while. The resultant was subjected to extraction with chloroform and washed 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, thereby obtaining the subject compound (317 mg) as a yellow oily substance.

Workup

  1. stirringin an ice bath, and the whole was stirred at room temperature for 1 hour
  2. customAfter completion of the reaction
  3. distillationdistilled water
  4. additionwas added
  5. stirringthe whole was stirred for a while
  6. extractionThe resultant was subjected to extraction with chloroform
  7. washwashed 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

Sources & evidence

ORD record
ord-b88b98c73de8459f89107c5dc158bec0
Source dataset
uspto-grants-2011_04
Patent number
US07932281B2

Reaction notes

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