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

HRID 607413Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 607413
[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]

Komponenten

4

Edukt 2

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

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%).

Aufarbeitung

  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)

Quellen und Nachweise

ORD-Eintrag
ord-3e02e426c01345e4bf103dd30bd1352e
Quelldatensatz
uspto-grants-2011_03
Patentnummer
US07915443B2

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