Methanol → HCID 178441434, compound

HRID 1457780Notes

Reaction equation

HRID 1457780 reaction equation
[CH2:1]([C:5]1[N:21]([CH2:22][C:23]2[CH:28]=[CH:27][C:26]([C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=3[C:35]3[N:39](C(OCC)C)[N:38]=[N:37][N:36]=3)=[CH:25][CH:24]=2)[C:8]2=[N:9][C:10](C=O)=[C:11]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[CH:12]=[C:7]2[N:6]=1)[CH2:2][CH2:3][CH3:4].Cl.[CH3:46][OH:47].[C:48]([O-])(O)=O.[Na+].[CH3:53][OH:54]>>[CH2:1]([C:5]1[N:21]([CH2:22][C:23]2[CH:28]=[CH:27][C:26]([C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=3[C:35]3[NH:39][N:38]=[N:37][N:36]=3)=[CH:25][CH:24]=2)[C:8]2=[N:9][C:10]([CH:46]([O:54][CH3:53])[O:47][CH3:48])=[C:11]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[CH:12]=[C:7]2[N:6]=1)[CH2:2][CH2:3][CH3:4]

Participants

5

Reactant 4

HCID 887MethanolHCID 516892Sodium BicarbonateHCID 21893726Hydrochloride methanolHCID 22100380HCID 22100380, compound

Product 1

HCID 178441434HCID 178441434, compoundYield 79.4%

Procedure

0.1 g(0.000169 mole) of the compound obtained in step 11 and 0.36 g(0.00338 mole) of trimethylformate were dissolved in 5 ml of methanol and to the resulting solution was added 0.5 ml of 3% anhydrous HCl/MeOH. The resultant was refluxed for 2 hours and cooled. 5 ml of saturated NaHCO3 solution was added to the reaction solution. The resulting solution was evaporated under reduced pressure to remove methanol and thereafter extracted with ethyl acetate(5 ml×4). The organic layer was dried over Na2SO4 and concentrated under reduced pressure. The residue was recrystallized from hexane-methylene chloride to obtain 75 mg of the title compound in a white solid form(yield 79.4%).

Workup

  1. temperatureThe resultant was refluxed for 2 hours
  2. temperaturecooled
  3. customThe resulting solution was evaporated under reduced pressure
  4. customto remove methanol
  5. extractionextracted with ethyl acetate(5 ml×4)
  6. dry with materialThe organic layer was dried over Na2SO4
  7. concentrationconcentrated under reduced pressure
  8. customThe residue was recrystallized from hexane-methylene chloride

Sources & evidence

ORD record
ord-5e07f7ca67ca4307b1db84357e9f9c6a
Source dataset
uspto-grants-1998_12
Patent number
US05849753

Reaction notes

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