Trifluoromethanesulfonic anhydride → HCID 178500919, Verbindung

HRID 1063622

Reaktionsgleichung

Reaktionsgleichung von HRID 1063622
[OH:1][CH2:2][CH2:3][C:4]([O:6][CH3:7])=[O:5].C(C1C=CC=C(C(C)(C)C)N=1)(C)(C)C.FC(F)(F)S(OS(C(F)(F)F)(=O)=O)(=O)=O.O[C@H:38]1[CH2:43][CH2:42][C@H:41]([N:44]([CH3:58])[S:45]([C:48]2[CH:53]=[CH:52][C:51]([C:54]([F:57])([F:56])[F:55])=[CH:50][CH:49]=2)(=[O:47])=[O:46])[CH2:40][CH2:39]1>C(Cl)Cl.[N+](C)([O-])=O.CCOC(C)=O.OS([O-])(=O)=O.[K+]>[CH3:7][O:6][C:4](=[O:5])[CH2:3][CH2:2][O:1][C@H:38]1[CH2:39][CH2:40][C@H:41]([N:44]([CH3:58])[S:45]([C:48]2[CH:53]=[CH:52][C:51]([C:54]([F:56])([F:55])[F:57])=[CH:50][CH:49]=2)(=[O:47])=[O:46])[CH2:42][CH2:43]1

Komponenten

9

Edukt 4

HCID 67749Trifluoromethanesulfonic anhydrideHCID 685102,6-Di-tert-butylpyridine2×HCID 80252Propanoic acid, 3-hydroxy-, methyl esterHCID 178484845HCID 178484845, Verbindung

Produkt 1

HCID 178500919HCID 178500919, VerbindungAusbeute 95,7 %

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 6344DichloromethaneLösungsmittelHCID 6375NitromethaneLösungsmittelHCID 8857Ethyl AcetateLösungsmittelHCID 516920Potassium bisulfateLösungsmittel

Versuchsvorschrift

At 0° C. to a solution of 0.62 g (5.9 mmol) of methyl beta-hydroxypropionate in 4.5 mL of CH2Cl2 was added 1.4 mL (6.4 mmol, 2.4 eq) of 2,6-di-tert-butylpyridine, followed by 1.03 mL (6.2 mmol, 2.4 eq) of trifluoromethane sulfonic acid anhydride. The solution was stirred at that temperature for 2.5 h, was concentrated, and the residue was dissolved in 5 mL of nitromethane. To this solution 1 g (2.96 mmol) of trans-N-(4-hydroxy-cyclohexyl)-N-methyl-4-trifluoromethyl-benzenesulfonamide and 1.3 mL (5.9 mmol, 2.0 eq) of 2,6-di-tert-butylpyridine in 10 mL of nitromethane were added. The solution was stirred at 60° C. for 3 h, diluted with EtOAc and 1M KHSO4. The inorganic phase was extracted with EtOAc, the combined organic phases were washed with a saturated aqueous solution of NaHCO3, brine and were dried over Na2SO4 and evaporated. Column chromatography on silica gel with EtOAc/n-hexane 1:3 gave 1.2 g (95%) of trans-3-{4-[methyl-(4-trifluoromethyl-benzenesulfonyl)-amino]-cyclohexyloxy}-propionic acid methyl ester as light yellow oil, MS: 424 (MH+).

Aufarbeitung

  1. concentrationwas concentrated
  2. dissolutionthe residue was dissolved in 5 mL of nitromethane
  3. stirringThe solution was stirred at 60° C. for 3 h
  4. extractionThe inorganic phase was extracted with EtOAc
  5. washthe combined organic phases were washed with a saturated aqueous solution of NaHCO3, brine
  6. dry with materialwere dried over Na2SO4
  7. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-0ab0dbe7d73b40679dc1f0b713d0a990
Quelldatensatz
uspto-grants-2005_11
Patentnummer
US06965048B2

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