Triethylamine → HCID 9828351, compound

HRID 1418140Notes

Reaction equation

HRID 1418140 reaction equation
[Cl:1][C:2]1[CH:21]=[CH:20][C:5]([C:6]([O:8][CH2:9][C@H:10]2[O:15][CH:13]([OH:14])[C@H:12]([OH:16])[C@:11]2([C:18]#[CH:19])[OH:17])=[O:7])=[CH:4][CH:3]=1.C(N([CH2:27][CH3:28])CC)C.[C:29](Cl)(=[O:33])[O:30][CH2:31][CH3:32]>ClCCl.CN(C)C1C=CN=CC=1>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:6]([O:8][CH2:9][C@H:10]2[O:15][CH:13]([O:14][C:29]([O:30][CH2:31][CH3:32])=[O:33])[C@H:12]([O:16][C:6]([O:8][CH2:9][CH3:10])=[O:7])[C@:11]2([C:18]#[CH:19])[O:17][C:13]([O:15][CH2:27][CH3:28])=[O:14])=[O:7])=[CH:20][CH:21]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 10928Ethyl chloroformateHCID 53682078HCID 53682078, compound

Product 1

HCID 9828351HCID 9828351, compoundYield 167.8%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

The 5-O-(4-chlorobenzoyl)-3-C-ethynyl-D-ribofuranose (1.0 g; 3.20 mmol) obtained in Example 6 was suspended in dichloromethane (12 ml). To the resultant suspension were added 4-dimethylaminopyridine (12 mg; 0.098 mmol) and triethylamine (1.56 ml; 11.2 mmol). The mixture was cooled on ice. Ethyl chlorocarbonate (1.07 ml; 11.2 mmol) was added thereto and the liquid temperature was returned to room temperature. The mixture was stirred for one hour. The solvent was evaporated under reduced pressure. Ethyl acetate (40 ml) and water (40 ml) were added to the residue, then phases were separated. The ethyl acetate phase was washed once with saturated aqueous sodium hydrogencarbonate solution, then dried over magnesium sulfate. After filtration, the filtrate was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate:n-hexane=1:3), yielding 1.42 g (yield: 84.0%) of the title compound as a colorless oily substance.

Workup

  1. temperatureThe mixture was cooled on ice
  2. customwas returned to room temperature
  3. customThe solvent was evaporated under reduced pressure
  4. additionEthyl acetate (40 ml) and water (40 ml) were added to the residue
  5. customphases were separated
  6. washThe ethyl acetate phase was washed once with saturated aqueous sodium hydrogencarbonate solution
  7. dry with materialdried over magnesium sulfate
  8. filtrationAfter filtration
  9. customthe filtrate was evaporated under reduced pressure
  10. customThe residue was purified by silica gel column chromatography (ethyl acetate:n-hexane=1:3)

Sources & evidence

ORD record
ord-e5bdee2efcfa45ac81d42d09b3190466
Source dataset
uspto-grants-1999_03
Patent number
US05880294

Reaction notes

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