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

HRID 391581Notes

Reaction equation

HRID 391581 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-af2d4656b72d40e48d9ac3811dfd53e8
Source dataset
uspto-grants-2013_02
Patent number
US08383825B2

Reaction notes

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