Trifluoroacetamide → Methyl 3-{4-[S-methyl-N-(trifluoroacetyl)sulfonimidoyl]phenyl}-propanoate

HRID 1099670Notes

Reaction equation

HRID 1099670 reaction equation
[CH3:1][S:2]([C:4]1[CH:9]=[CH:8][C:7]([CH2:10][CH2:11][C:12]([O:14][CH3:15])=[O:13])=[CH:6][CH:5]=1)=[O:3].[F:16][C:17]([F:22])([F:21])[C:18]([NH2:20])=[O:19]>C(Cl)Cl>[CH3:1][S:2]([C:4]1[CH:5]=[CH:6][C:7]([CH2:10][CH2:11][C:12]([O:14][CH3:15])=[O:13])=[CH:8][CH:9]=1)(=[N:20][C:18](=[O:19])[C:17]([F:22])([F:21])[F:16])=[O:3]

Participants

4

Reactant 2

HCID 67717TrifluoroacetamideHCID 57657897Methyl 3-(4-(methylsulfinyl)phenyl)propanoate

Product 1

HCID 57657821Methyl 3-{4-[S-methyl-N-(trifluoroacetyl)sulfonimidoyl]phenyl}-propanoateYield 69%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

In a 100 mL round bottom flask, methyl 3-(4-(methylsulfinyl)phenyl)propanoate (0.4 g, 1.77 mmol) was added to CH2Cl2 (18 mL). Subsequently the reaction was treated with MgO (0.285 g, 7.08 mmol), trifluoroacetamide (0.400 g, 3.54 mmol), PhI(OAc)4 (0.884 g, 2.66 mmol), and Rh2(OAc)4 (19.55 mg, 0.0443 mmol). The suspension was stirred overnight then filtered through celite. The filtrate was the concentrated. The resulting residue was purified via column chromatography (silica gel, gradient eluant mixture: 20% EtOAc in hexanes to 100% EtOAc) to give the title compound (0.294 g, 69%).

Workup

  1. filtrationthen filtered through celite
  2. customThe resulting residue was purified via column chromatography (silica gel, gradient eluant mixture: 20% EtOAc in hexanes to 100% EtOAc)

Sources & evidence

ORD record
ord-9ee2483247b4458bb1f6cfceedf22bb1
Source dataset
uspto-grants-2012_03
Patent number
US08143410B2

Reaction notes

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