2,6-Lutidine → HCID 54442206, compound

HRID 1736016Notes

Reaction equation

HRID 1736016 reaction equation
O[CH:2]1[C:7]2[CH:8]=[C:9]([S:11]([NH:14][C:15]([CH3:18])([CH3:17])[CH3:16])(=[O:13])=[O:12])[S:10][C:6]=2[S:5](=[O:20])(=[O:19])[N:4]([CH2:21][CH:22]=[CH:23][CH2:24][N:25]2[CH2:30][CH2:29][O:28][CH2:27][CH2:26]2)[CH2:3]1.CS(OS(C)(=O)=O)(=O)=O.N1C(C)=CC=CC=1C.C1CN2C(=NCCC2)C1.C(=O)(O)[O-].[Na+]>C1COCC1.CN(C=O)C>[CH3:18][C:15]([NH:14][S:11]([C:9]1[S:10][C:6]2[S:5](=[O:20])(=[O:19])[N:4]([CH2:21][CH:22]=[CH:23][CH2:24][N:25]3[CH2:26][CH2:27][O:28][CH2:29][CH2:30]3)[CH:3]=[CH:2][C:7]=2[CH:8]=1)(=[O:12])=[O:13])([CH3:16])[CH3:17]

Participants

8

Reactant 5

HCID 79372,6-Lutidine2×HCID 763491,5-Diazabicyclo(4.3.0)non-5-eneHCID 81560Methanesulfonic anhydride2×HCID 516892Sodium BicarbonateHCID 54423361HCID 54423361, compound

Product 1

HCID 54442206HCID 54442206, compoundYield 57%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of the product from Step A (0.64 g, 1.34 mmol) in anhydrous THF (30 mL) under nitrogen were added methanesulfonic anhydride (0.349 g, 2.00 mmol) and 2,6-lutidine (0.431 g, 4.02 mmol). After 30 min, an additional quantity of methanesulfonic anhydride (0.349 g, 2.00 mmol) and 2,6-lutidine (0.431 g, 4.02 mmol) was added and the reaction continued for 30 min. Evaporation of the solvent provided a residue which was dissolved in anhydrous DMF (50 mL) and DBN (1 mL) was added. This mixture was heated at reflux temperature for 1 h, cooled, poured into a saturated solution of sodium bicarbonate (100 mL) and extracted with ethyl acetate (2×100 mL). The combined extracts were dried over (MgSO4), filtered and evaporated to a residue which was purified by column chromatography (silica, 5% methanol/methylene chloride) to give a viscous oil (0.35 g, 57%).

Workup

  1. waitthe reaction continued for 30 min
  2. customEvaporation of the solvent
  3. customprovided a residue which
  4. temperatureThis mixture was heated
  5. temperatureat reflux temperature for 1 h
  6. temperaturecooled
  7. extractionextracted with ethyl acetate (2×100 mL)
  8. dry with materialThe combined extracts were dried over (MgSO4)
  9. filtrationfiltered
  10. customevaporated to a residue which
  11. customwas purified by column chromatography (silica, 5% methanol/methylene chloride)

Sources & evidence

ORD record
ord-4003ba9123aa469aaebcc0d85f55fa05
Source dataset
uspto-grants-1996_07
Patent number
US05538966

Reaction notes

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