Dichloromethane → HCID 54356446, compound

HRID 279061Notes

Reaction equation

HRID 279061 reaction equation
S1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=[N:2]1.C[N+]1([O-])CCOCC1.[S:16](=[O:20])(=O)(O)[O-:17].[Na+].C(Cl)Cl>O.CC(C)=O.CC(O)(C)C.[Os](=O)(=O)(=O)=O>[S:16]1(=[O:20])(=[O:17])[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=[N:2]1

Participants

8

Reactant 4

HCID 6344DichloromethaneHCID 82029Methyl morpholine oxideHCID 516919Sodium BisulfateHCID 12444276HCID 12444276, compound

Product 1

HCID 54356446HCID 54356446, compoundYield 83%

Reagents, catalysts & solvents 3

HCID 30318Osmium TetroxideCatalystHCID 6386tert-ButanolSolventHCID 18366337Propan-2-one--water (1/1)Solvent

Procedure

To a stirred solution of the thiazepine prepared in Step 8 of Example 482 (243.7 mg) in 25% H2O/acetone (8 mL) is added 4-methylmorpholine N-oxide (201.5 mg) followed by a solution of osmium tetroxide in 2-methyl-2-propanol (2.5 wt %, 30 μL). The reaction mixture is stirred at room temperature for 18 h. The reaction mixture is treated with saturated sodium bisulfate (8 mL), then poured into CH2Cl2 (50 mL). The phases are separated. The aqueous phase is extracted with CH2Cl2 (2×25 mL). The combined organic phases are washed with brine (1×25 mL), dried (MgSO4), filtered and concentrated. The residue is purified on a Biotage 40 S column using 1% CH3OH in CH2Cl2 as the eluent to afford 216.1 mg (0.47 mmol, 83%) of the thiazepine S,S-dioxide as a white solid. mp 144-146° C.

Workup

  1. customThe phases are separated
  2. extractionThe aqueous phase is extracted with CH2Cl2 (2×25 mL)
  3. washThe combined organic phases are washed with brine (1×25 mL)
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue is purified on a Biotage 40 S column

Sources & evidence

ORD record
ord-70a82aedfee6405a8873c250591b980f
Source dataset
uspto-grants-2002_03
Patent number
US06362189B1

Reaction notes

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