Water → HCID 69801849, compound

HRID 1976388Notes

Reaction equation

HRID 1976388 reaction equation
C[N:2]1[CH2:7][CH2:6][O:5][CH2:4][CH2:3]1.[F:8][C:9]1[CH:14]=[CH:13][C:12]([S:15](Cl)(=[O:17])=[O:16])=[CH:11][CH:10]=1.[OH2:19]>ClCCl>[F:8][C:9]1[CH:14]=[CH:13][C:12]([S:15]([N:2]2[CH2:3][CH2:4][S:15][C:12]([CH3:13])([CH3:11])[C@@H:7]2[C:6]([OH:5])=[O:19])(=[O:17])=[O:16])=[CH:11][CH:10]=1

Participants

5

Reactant 3

HCID 962WaterHCID 79724-MethylmorpholineHCID 95884-Fluorobenzenesulfonyl chloride

Product 1

HCID 69801849HCID 69801849, compoundYield 40%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a 0° solution of 1.00 g (3.155 mmol) of 3-(S)-dimethylthexylsilyl-2,2-dimethyl-tetrahydro-2H-1,4thiazine-3-carboxylate (prepared as described in PCT patent application WO9720824) in 20 mL of dichloromethane was added 0.693 mL (6.85 mmol) of 4-methylmorpholine followed by 0.606 g (3.114 mmol) of 4-fluorobenzenesulfonyl chloride. The reaction was allowed to warm to room temperature and then stirred oveniight The reaction mixture was then poured into water and the organic layer was washed with water, dried over Na2SO4, filtered and concentrated in vacuo. The residue was dissolved in 20 mL of methanol and the solution was heated to reflux for 1 h and then concentrated in vacuo. The residue was then chromatographed on silica gel eluting with ethyl acetate/hexanes (1:3) to provide 0.385 g (40%) of the sulfonamide as a white foam. Electrospray Mass Spec 331.8 (M−H)−

Workup

  1. washthe organic layer was washed with water
  2. dry with materialdried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. dissolutionThe residue was dissolved in 20 mL of methanol
  6. temperaturethe solution was heated
  7. temperatureto reflux for 1 h
  8. concentrationconcentrated in vacuo
  9. customThe residue was then chromatographed on silica gel eluting with ethyl acetate/hexanes (1:3)

Sources & evidence

ORD record
ord-a27a122b39d8476ab77dd6c57eb05569
Source dataset
uspto-grants-2001_05
Patent number
US06225311B1

Reaction notes

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