Carbon Dioxide → HCID 178499648, compound

HRID 432067Notes

Reaction equation

HRID 432067 reaction equation
[OH:1][C:2]1[N:7]=[C:6]([NH:8][C:9](=[O:13])[CH:10]([CH3:12])[CH3:11])[N:5]=[C:4]2[NH:14][N:15]=[CH:16][C:3]=12.[H-].[Na+].Br[CH2:20][C:21]([O:23][CH3:24])=[O:22].C(=O)=O>CN(C=O)C.CO>[OH:1][C:2]1[N:7]=[C:6]([NH:8][C:9](=[O:13])[CH:10]([CH3:12])[CH3:11])[N:5]=[C:4]2[NH:14][N:15]=[C:16]([CH2:20][C:21]([O:23][CH3:24])=[O:22])[C:3]=12

Participants

7

Reactant 4

HCID 280Carbon DioxideHCID 24758Sodium hydrideHCID 60984Methyl bromoacetateHCID 178454504HCID 178454504, compound

Product 1

HCID 178499648HCID 178499648, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6228DimethylformamideSolvent

Procedure

Compound 16 (4.42 g; 20 mmole) is suspended in dry DMF (40 ml), sodium hydride (0.5 g; 20.8 mmole) is added in portions, and the mixture is stirred at room temperature for 60 min. Methyl bromoacetate (1.9 ml; 20.6 mmole) is then added at room temperature, by syringe, and stirring is continued at room temperature. At completion of the reaction (monitored by TLC), the reaction mixture is treated with a small amount of carbon dioxide in methanol. The solvent is then evaporated and the residue dissolved in CH2Cl2, washed once with water and then evaporated to dryness. The product is purified by chromatography to yield the desired isomer (17).

Workup

  1. stirringstirring
  2. customis continued at room temperature
  3. customAt completion of the reaction (monitored by TLC)
  4. customThe solvent is then evaporated
  5. dissolutionthe residue dissolved in CH2Cl2
  6. washwashed once with water
  7. customevaporated to dryness
  8. customThe product is purified by chromatography

Sources & evidence

ORD record
ord-e5b59c8802714ef883e13c953560ccd1
Source dataset
uspto-grants-2003_12
Patent number
US06660845B1

Reaction notes

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