Methyl chloroformate → HCID 9904929, compound

HRID 1613155Notes

Reaction equation

HRID 1613155 reaction equation
[CH3:1][NH:2][C:3]1[C:7]2[C:8](=[O:19])[N:9]([CH2:16][CH2:17][CH3:18])[C:10]3[CH:11]=[CH:12][CH:13]=[CH:14][C:15]=3[C:6]=2[NH:5][N:4]=1.[H-].[Na+].[C:22](Cl)(=[O:25])[O:23][CH3:24]>CN(C=O)C>[CH3:24][O:23][C:22]([N:5]1[C:6]2[C:15]3[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=3[N:9]([CH2:16][CH2:17][CH3:18])[C:8](=[O:19])[C:7]=2[C:3]([NH:2][CH3:1])=[N:4]1)=[O:25]

Participants

5

Reactant 3

HCID 6586Methyl chloroformateHCID 24758Sodium hydrideHCID 19775367HCID 19775367, compound

Product 1

HCID 9904929HCID 9904929, compoundYield 50%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

In 70 ml of DMF was suspended 1.69 g (6.6 mmol) of Compound 1, and 0.33 g (8.3 mmol) of 60% sodium hydride was added and dissolved therein. To the mixture was added 0.80 ml (10 mmol) of methyl chlorocarbonate, followed by stirring at room temperature for 1 hour. The reaction mixture was dried under reduced pressure, and the residue was partitioned between chloroform and water. The chloroform layer was dried under reduced pressure, passed through a silica gel column, and eluted with chloroform. The main fraction collected was dried under reduced pressure and recrystallized from water-containing ethanol to obtain 1.03 g (50%) of the titled compound as a colorless crystal.

Workup

  1. additionwas added
  2. dissolutiondissolved
  3. customThe reaction mixture was dried under reduced pressure
  4. customthe residue was partitioned between chloroform and water
  5. dry with materialThe chloroform layer was dried under reduced pressure
  6. washeluted with chloroform
  7. customThe main fraction collected
  8. customwas dried under reduced pressure
  9. customrecrystallized from water-
  10. additioncontaining ethanol

Sources & evidence

ORD record
ord-aaec1583598e4dfbb60fee7b6da5b38c
Source dataset
uspto-grants-1993_03
Patent number
US05192768

Reaction notes

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