Triethylamine → HCID 19434133, compound

HRID 1736034Notes

Reaction equation

HRID 1736034 reaction equation
[CH2:1]([O:3][CH:4]([O:6][CH2:7][CH2:8][CH2:9][CH2:10][N:11]1[C:16]([CH2:17]O)=[CH:15][C:14]2[CH:19]=[CH:20][S:21][C:13]=2[S:12]1(=[O:23])=[O:22])[CH3:5])[CH3:2].[CH2:24]([N:26](CC)[CH2:27][CH3:28])[CH3:25].CS(OS(C)(=O)=O)(=O)=[O:33]>C1COCC1>[CH2:1]([O:3][CH:4]([O:6][CH2:7][CH2:8][CH2:9][CH2:10][N:11]1[C:16]([CH2:17][N:26]2[CH2:27][CH2:28][O:33][CH2:25][CH2:24]2)=[CH:15][C:14]2[CH:19]=[CH:20][S:21][C:13]=2[S:12]1(=[O:23])=[O:22])[CH3:5])[CH3:2]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 81560Methanesulfonic anhydrideHCID 19434053HCID 19434053, compound

Product 1

HCID 19434133HCID 19434133, compoundYield 84%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of the product from Step C (2.52 g, 6.98 mmol) and triethylamine (1.41 g, 13.9 mmol) in anhydrous THF (20 mL) at 0° C. was added methanesulfonic anhydride (1.58 g, 9.07 mmol). The ice bath was removed and the reaction mixture was allowed to proceed for 20 min; the reaction mixture was again cooled on ice and morpholine (5 mL) was added. This mixture was stirred for 3 h at ambient temperature, evaporated to dryness and extracted with ethyl acetate (2×100). The combined extracts were dried (MgSO4), evaporated to dryness and purified by column chromatography (silica, 50% ethyl acetate/hexane) to give an oil (2.52 g, 84%).

Workup

  1. customThe ice bath was removed
  2. temperaturethe reaction mixture was again cooled on ice and morpholine (5 mL)
  3. additionwas added
  4. customevaporated to dryness
  5. extractionextracted with ethyl acetate (2×100)
  6. dry with materialThe combined extracts were dried (MgSO4)
  7. customevaporated to dryness
  8. custompurified by column chromatography (silica, 50% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-fef90da36b044b8881bd9001cbf9678d
Source dataset
uspto-grants-1996_07
Patent number
US05538966

Reaction notes

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