Trifluoroacetic acid → (R)-5-(5-bromo-2-fluoro-phenyl)-5-methyl-1,1-dioxo-1lambda6-thiomorpholin-3-one

HRID 920161Notes

Reaction equation

HRID 920161 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([F:29])=[C:6]([C@@:8]2([CH3:28])[N:13](CC3C=CC(OC)=CC=3OC)[C:12](=[O:25])[CH2:11][S:10](=[O:27])(=[O:26])[CH2:9]2)[CH:7]=1.FC(F)(F)C(O)=O.C([O-])([O-])=O.[Na+].[Na+]>>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([F:29])=[C:6]([C@@:8]2([CH3:28])[NH:13][C:12](=[O:25])[CH2:11][S:10](=[O:27])(=[O:26])[CH2:9]2)[CH:7]=1

Participants

4

Reactant 3

HCID 6422Trifluoroacetic acidHCID 10340Sodium CarbonateHCID 90067087(R)-5-(5-bromo-2-fluoro-phenyl)-4-(2,4-dimethoxy-benzyl)-5-methyl-1,1-dioxo-1lambda6-thiomorpholin-3-one

Product 1

HCID 90067097(R)-5-(5-bromo-2-fluoro-phenyl)-5-methyl-1,1-dioxo-1lambda6-thiomorpholin-3-oneYield 66.9%

Conditions

Temperature
23 °C

Procedure

A mixture of (R)-5-(5-bromo-2-fluoro-phenyl)-4-(2,4-dimethoxy-benzyl)-5-methyl-1,1-dioxo-1λ6-thiomorpholin-3-one (251 mg, 516 μmol, Eq: 1.00) and trifluoroacetic acid (5.88 g, 3.98 ml, 51.6 mmol, Eq: 100) was stirred at 23° C. for 16 hours. Poured into 1 M Na2CO3-sol. and extracted twice with ethyl acetate. The combined organic layers were dried over Na2SO4, filtered and evaporated. The residue was chromatographed on 5 g silica gel with dichloromethane/ethyl acetate 9:1 to give (R)-5-(5-bromo-2-fluoro-phenyl)-5-methyl-1,1-dioxo-1λ6-thiomorpholin-3-one (116 mg, 345 μmol, 66.9% yield) as a white solid. MS (ISN): m/z=334.0 [M−H]− and 336.0 [M+2−H]−.

Workup

  1. extractionand extracted twice with ethyl acetate
  2. dry with materialThe combined organic layers were dried over Na2SO4
  3. filtrationfiltered
  4. customevaporated
  5. customThe residue was chromatographed on 5 g silica gel with dichloromethane/ethyl acetate 9:1

Sources & evidence

ORD record
ord-d8ecc100eb2a4111be10463de92d3415
Source dataset
uspto-grants-2016_03
Patent number
US09273042B2

Reaction notes

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