Ethyl Acetate → 3-(3-tert-Butoxycarbonyl-propylsulfanyl)-5-trifluoromethyl-benzoic acid methyl ester

HRID 403390

Reaktionsgleichung

Reaktionsgleichung von HRID 403390
[CH3:1][O:2][C:3](=[O:15])[C:4]1[CH:9]=[C:8]([C:10]([F:13])([F:12])[F:11])[CH:7]=[C:6]([SH:14])[CH:5]=1.C(N(CC)C(C)C)(C)C.Br[CH2:26][CH2:27][CH2:28][C:29]([O:31][C:32]([CH3:35])([CH3:34])[CH3:33])=[O:30].C(OCC)(=O)C>C(#N)C>[CH3:1][O:2][C:3](=[O:15])[C:4]1[CH:9]=[C:8]([C:10]([F:12])([F:13])[F:11])[CH:7]=[C:6]([S:14][CH2:26][CH2:27][CH2:28][C:29]([O:31][C:32]([CH3:35])([CH3:34])[CH3:33])=[O:30])[CH:5]=1

Komponenten

6

Edukt 4

HCID 8857Ethyl AcetateHCID 81531DiisopropylethylamineHCID 2757253tert-Butyl 4-bromobutanoateHCID 68203827Benzoic acid, 3-mercapto-5-(trifluoromethyl)-, methyl ester

Produkt 1

HCID 682038283-(3-tert-Butoxycarbonyl-propylsulfanyl)-5-trifluoromethyl-benzoic acid methyl ester

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

To a solution of 3-mercapto-5-trifluoromethyl-benzoic acid methyl ester (990 mg, 4.19 mmol) in acetonitrile (25 mL) were added N,N-diisopropylethylamine (1.08 g, 1.46 mL, 8.38 mmol) and tert-butyl 4-bromobutanoate (935 mg, 4.19 mmol, CAS RN 110611-91-1). The clear yellow solution was stirred at room temperature for 2.5 hours and then poured on water and ethyl acetate and the layers were separated. The aqueous layer was extracted twice with ethyl acetate. The organic layers were washed with brine, dried over magnesium sulfate, filtered, treated with silica gel and evaporated. The compound was purified by silica gel chromatography on a 50 g column using a MPLC system (CombiFlash Companion, Isco Inc.) eluting with a gradient of n-heptane:ethyl acetate (100:0 to 70:30). Light yellow liquid (1.27 g, 80%). MS (ESI+): m/z=379 ([M+]).

Aufarbeitung

  1. customthe layers were separated
  2. extractionThe aqueous layer was extracted twice with ethyl acetate
  3. washThe organic layers were washed with brine
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. additiontreated with silica gel
  7. customevaporated
  8. customThe compound was purified by silica gel chromatography on a 50 g column
  9. washeluting with a gradient of n-heptane:ethyl acetate (100:0 to 70:30)

Quellen und Nachweise

ORD-Eintrag
ord-448051f2358b4aeab4e59db3d63c93fb
Quelldatensatz
uspto-grants-2014_06
Patentnummer
US08748434B2

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