Methanesulfonic anhydride → HCID 21480486, compound

HRID 1490054Notes

Reaction equation

HRID 1490054 reaction equation
CS(OS(C)(=O)=O)(=O)=O.C(O[CH:13]([O:15][CH2:16][CH:17]1[CH2:31][N:21]2[S:22](=[O:30])(=[O:29])[C:23]3[S:28][CH:27]=[CH:26][C:24]=3[CH:25]=[C:20]2[CH2:19][NH:18]1)[CH3:14])C>C1COCC1>[CH3:14][CH:13]1[N:18]2[CH2:19][C:20]3[N:21]([CH2:31][CH:17]2[CH2:16][O:15]1)[S:22](=[O:30])(=[O:29])[C:23]1[S:28][CH:27]=[CH:26][C:24]=1[CH:25]=3

Participants

4

Reactant 2

HCID 81560Methanesulfonic anhydrideHCID 21480496HCID 21480496, compound

Product 1

HCID 21480486HCID 21480486, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Methane sulfonic anhydride (0.78 g, 4.53 mmol) was added to a solution of the product of Step F (1,3 g, 3.78 mmol) in THF (40 mL) at 0° C. This mixture was stirred for 1 h and then allowed to warm to room temperature and stirred for an additional 2 h. The reaction mixture was washed with a saturated solution of sodium bicarbonate and extracted with ethyl acetate (3×100mL). The combined extracts were dried (MgSO4) and evaporated to a residue which was purified by column chromatography (silica, acetone/hexane, 1:1) to give 1 g (83%) of an off white amorphous solid.

Workup

  1. stirringstirred for an additional 2 h
  2. washThe reaction mixture was washed with a saturated solution of sodium bicarbonate
  3. extractionextracted with ethyl acetate (3×100mL)
  4. dry with materialThe combined extracts were dried (MgSO4)
  5. customevaporated to a residue which
  6. customwas purified by column chromatography (silica, acetone/hexane, 1:1)
  7. customto give 1 g (83%) of an off white amorphous solid

Sources & evidence

ORD record
ord-a155f9e5a3404471b3b937eb447a0176
Source dataset
uspto-grants-1997_10
Patent number
US05681834

Reaction notes

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