Cesium carbonate → HCID 54294189, compound

HRID 745772Notes

Reaction equation

HRID 745772 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[N:7]=[CH:8][C:9]2[NH:10][C:11]3[C:16]([C:17]=2[C:18]=1[CH2:19][O:20][CH3:21])=[CH:15][C:14]([C:22]([OH:24])=[O:23])=[CH:13][CH:12]=3)=[O:5])[CH3:2].[C:25](=O)([O-])[O-].[Cs+].[Cs+]>C(O)C.O>[CH2:1]([O:3][C:4]([C:6]1[N:7]=[CH:8][C:9]2[NH:10][C:11]3[C:16]([C:17]=2[C:18]=1[CH2:19][O:20][CH3:21])=[CH:15][C:14]([C:22]([O:24][CH3:25])=[O:23])=[CH:13][CH:12]=3)=[O:5])[CH3:2]

Participants

5

Reactant 2

HCID 10796Cesium carbonateHCID 23312162HCID 23312162, compound

Product 1

HCID 54294189HCID 54294189, compoundYield 43.7%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent2×

Procedure

202 mg of 3-ethoxycarbonyl-4-methoxymethyl-β-carboline-6-carboxylic acid is combined in 15 ml of ethanol and 5 ml of water with 206 mg of cesium carbonate in 1.5 ml of water and stirred until a clear solution is obtained. The solution is then evaporated to dryness, taken up in 10 ml of dimethylformamide, 0.14 ml of methyl iodide is added, and the mixture is agitated at room temperature for 3 hours. After evaporation, the mixture is distributed in methylene chloride/saturated sodium chloride solution. The organic phase is dried, filtered, concentrated, and chromatographed over silica gel with methylene chloride/ethanol=6:1 as the eluent. After recrystallization of the corresponding fractions from ethanol/hexane, 92 mg of 6-methoxycarbonyl-4-methoxymethyl-β-carboline-3-carboxylic acid ethyl ester is obtained.

Workup

  1. customis obtained
  2. customThe solution is then evaporated to dryness
  3. addition0.14 ml of methyl iodide is added
  4. customAfter evaporation
  5. customThe organic phase is dried
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customchromatographed over silica gel with methylene chloride/ethanol=6:1 as the eluent
  9. customAfter recrystallization of the corresponding fractions from ethanol/hexane

Sources & evidence

ORD record
ord-f6b6670910cb4f6eace092b9b8403c43
Source dataset
uspto-grants-1986_07
Patent number
US04600715

Reaction notes

Loading…