Methyl chloroformate → HCID 19775365, compound

HRID 1613156Notes

Reaction equation

HRID 1613156 reaction equation
[CH2:1]([NH:5][C:6]1[C:10]2[C:11](=[O:22])[N:12]([CH2:19][CH2:20][CH3:21])[C:13]3[CH:14]=[CH:15][CH:16]=[CH:17][C:18]=3[C:9]=2[NH:8][N:7]=1)[CH2:2][CH2:3][CH3:4].C(N(CC)CC)C.[C:30](Cl)(=[O:33])[O:31][CH3:32]>O1CCOCC1>[CH2:1]([NH:5][C:6]1[C:10]2[C:11](=[O:22])[N:12]([CH2:19][CH2:20][CH3:21])[C:13]3[CH:14]=[CH:15][CH:16]=[CH:17][C:18]=3[C:9]=2[N:8]([C:30]([O:31][CH3:32])=[O:33])[N:7]=1)[CH2:2][CH2:3][CH3:4]

Participants

5

Reactant 3

HCID 6586Methyl chloroformateHCID 8471TriethylamineHCID 19775369HCID 19775369, compound

Product 1

HCID 19775365HCID 19775365, compoundYield 40%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

In 60 ml of dioxane was suspended 1.40 g (4.7 mmol) of Compound 2, and 1.0 ml (7.2 mmol) of triethylamine and 0.73 ml (9.4 mmol) of methyl chlorocarbonate were added thereto, followed by stirring at room temperature for 2 hours. 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, and the residue was passed through a silica gel column and eluted with a 3:1 (by volume) mixed solvent of hexane and ethyl acetate. The main fraction collected was recrystallized from hexane-ethyl acetate to obtain 0.67 g (40%) of the titled compound as a colorless crystal.

Workup

  1. additionwere added
  2. customThe reaction mixture was dried under reduced pressure
  3. customthe residue was partitioned between chloroform and water
  4. dry with materialThe chloroform layer was dried under reduced pressure
  5. washeluted with a 3:1 (by volume)
  6. additionmixed solvent of hexane and ethyl acetate
  7. customThe main fraction collected
  8. customwas recrystallized from hexane-ethyl acetate

Sources & evidence

ORD record
ord-2900c4b188f044f2b4562411f20fdb84
Source dataset
uspto-grants-1993_03
Patent number
US05192768

Reaction notes

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