HCID 21836543, compound → Benzyl 1,1-dioxo-1lambda~6~,4-thiazinane-4-carboxylate

HRID 860492Notes

Reaction equation

HRID 860492 reaction equation
[N:1]1([C:7]([O:9][CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[O:8])[CH2:6][CH2:5]S[CH2:3][CH2:2]1.O[O:18][S:19]([O-:21])=O.[K+]>CO.O>[N:1]1([C:7]([O:9][CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[O:8])[CH2:2][CH2:3][S:19](=[O:21])(=[O:18])[CH2:5][CH2:6]1

Participants

5

Reactant 2

HCID 21836543HCID 21836543, compoundHCID 23707502Potassium hydroxy sulfite

Product 1

HCID 21836497Benzyl 1,1-dioxo-1lambda~6~,4-thiazinane-4-carboxylateYield 69.8%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

To a solution of benzyl 4-thiomorpholinecarboxylate (4.8 g) in methanol (30 mL) and H2O (20 mL) was added oxone (16.2 g) under ice water cooling and the mixture was stirred at ambient temperature for 2 hours. The solution was evaporated in vacuo and partitioned between EtOAc and water. The aqueous layer was extracted with EtOAc. The combined organic layer was washed with water and brine, dried over MgSO4 and evaporated in vacuo. The residue was purified by silica gel column chromatography eluting with a mixture of hexane and EtOAc to give benzyl 4-thiomorpholinecarboxylate 1,1-dioxide as a colorless solid (3.8 g).

Workup

  1. customThe solution was evaporated in vacuo
  2. custompartitioned between EtOAc and water
  3. extractionThe aqueous layer was extracted with EtOAc
  4. washThe combined organic layer was washed with water and brine
  5. dry with materialdried over MgSO4
  6. customevaporated in vacuo
  7. customThe residue was purified by silica gel column chromatography
  8. washeluting with a mixture of hexane and EtOAc

Sources & evidence

ORD record
ord-7a1e27e969164e87bee0825720cfa23e
Source dataset
uspto-grants-2006_12
Patent number
US07153854B2

Reaction notes

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