Triethylamine → HCID 19434030, compound

HRID 1736006Notes

Reaction equation

HRID 1736006 reaction equation
O[CH2:2][CH2:3][N:4]1[CH:9]=[CH:8][C:7]2[CH:10]=[C:11]([S:13]([NH:16][C:17]([CH3:20])([CH3:19])[CH3:18])(=[O:15])=[O:14])[S:12][C:6]=2[S:5]1(=[O:22])=[O:21].C([N:25]([CH2:28][CH3:29])CC)C.[CH3:30]S(OS(C)(=O)=O)(=O)=O>C1COCC1.CN(C=O)C.C(N)CC>[CH2:28]([NH:25][CH2:2][CH2:3][N:4]1[CH:9]=[CH:8][C:7]2[CH:10]=[C:11]([S:13]([NH:16][C:17]([CH3:20])([CH3:19])[CH3:18])(=[O:15])=[O:14])[S:12][C:6]=2[S:5]1(=[O:22])=[O:21])[CH2:29][CH3:30]

Participants

7

Reactant 3

HCID 8471TriethylamineHCID 81560Methanesulfonic anhydrideHCID 19434124HCID 19434124, compound

Product 1

HCID 19434030HCID 19434030, compoundYield 102.9%

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideSolventHCID 7852PropylamineSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of the product from Example 7, Step B (1.02 g, 2.79 mmol) and triethylamine (0.84 g, 8.36 mmol) in anhydrous THF (50 mL) was added methanesulfonic anhydride (0.80 g, 4.18 mmol) with stirring under nitrogen. The volatiles were evaporated after 30 min and the residue dissolved in ethyl acetate (80 mL). This mixture was washed with a saturated aqueous solution of sodium bicarbonate (50 mL), dried (MgSO4) and evaporated to give a solid. The solid (1.55 g from two batches) was dissolved in a mixture of anhydrous DMF (40 mL) and 1-propylamine (6 mL) and heated at reflux temperature for 1 h followed by evaporation to a residue which was added to a saturated aqueous solution of sodium bicarbonate (100 mL). This mixture was extracted with ethyl acetate (2×100 mL) and the combined extracts were dried (MgSO4) and evaporated to an oil which was purified by column chromatography (silica, 6% methanol/methylene chloride) to give a viscous oil (1.17 g, 84%).

Workup

  1. customThe volatiles were evaporated after 30 min
  2. dissolutionthe residue dissolved in ethyl acetate (80 mL)
  3. washThis mixture was washed with a saturated aqueous solution of sodium bicarbonate (50 mL)
  4. dry with materialdried (MgSO4)
  5. customevaporated
  6. customto give a solid
  7. temperatureheated
  8. temperatureat reflux temperature for 1 h
  9. customfollowed by evaporation to a residue which
  10. additionwas added to a saturated aqueous solution of sodium bicarbonate (100 mL)
  11. extractionThis mixture was extracted with ethyl acetate (2×100 mL)
  12. dry with materialthe combined extracts were dried (MgSO4)
  13. customevaporated to an oil which
  14. customwas purified by column chromatography (silica, 6% methanol/methylene chloride)

Sources & evidence

ORD record
ord-3925b39bf9404b35927220779f33da41
Source dataset
uspto-grants-1996_07
Patent number
US05538966

Reaction notes

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