Trifluoroacetamide → dimethyl 2,2'[N-(trifluoroacetyl)sulfonimidoyl]diacetate

Trifluoroacetamide (5.43 g, 2 eq), magnesium oxide (3.756 g, 4 eq), and rhodium(II) acetate dimer (309 mg, 0.03 eq) were placed in a 500 mL round-bottom flask. Dichloromethane (230 mL) was added followed by dimethyl 2,2′-sulfinyldiacetate (4.52 g, 23.3 mmol, 1 eq), followed by addition of diacetoxyiodobenzene in small portions (11.257 g, 1.5 eq). The mixture was stirred at room temperature for 7 hours. Following that, an additional 2.2 g of trifluoroacetamide was added followed by the addition of additional amount of rhodium(II) acetate dimer (˜150 mg) and diacetoxyiodobenzene (3.0 g). The reaction mixture was stirred further at room temperature overnight. The mixture was then filtered through a pad of celite and the pad was washed with MeOH—CHCl3 (1:5). The filtrate was concentrated and the oily residue was subject to column chromatography twice (from hexane to EtOAc-Hex 1:1) yielding dimethyl 2,2′-[N-(trifluoroacetyl)sulfonimidoyl]diacetate as a brown oil (7.0 g).

1. additionwas added
2. stirringThe reaction mixture was stirred further at room temperature overnight
3. filtrationThe mixture was then filtered through a pad of celite
4. washthe pad was washed with MeOH—CHCl3 (1:5)
5. concentrationThe filtrate was concentrated

ORD record

ord-71be56af3dd44a28968c6b98b1063407

Source dataset

uspto-grants-2013_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08558002B2