(+/-)-N-((5-benzyl-2-(2,5-difluorophenyl)oxazol-4-yl)methylene)-2-methylpropane-2-sulfinamide → (+/-)-N-(1-(5-benzyl-2-(2,5-difluorophenyl)oxazol-4-yl)-2,2-dimethylpropyl)-2-methylpropane-2-sulfinamide

HRID 404850Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 404850
[CH2:1]([C:8]1[O:12][C:11]([C:13]2[CH:18]=[C:17]([F:19])[CH:16]=[CH:15][C:14]=2[F:20])=[N:10][C:9]=1[CH:21]=[N:22][S:23]([C:25]([CH3:28])([CH3:27])[CH3:26])=[O:24])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Li][C:30]([CH3:33])([CH3:32])[CH3:31]>C1COCC1>[CH2:1]([C:8]1[O:12][C:11]([C:13]2[CH:18]=[C:17]([F:19])[CH:16]=[CH:15][C:14]=2[F:20])=[N:10][C:9]=1[CH:21]([NH:22][S:23]([C:25]([CH3:28])([CH3:27])[CH3:26])=[O:24])[C:30]([CH3:33])([CH3:32])[CH3:31])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Komponenten

4

Edukt 2

HCID 67451222(+/-)-N-((5-benzyl-2-(2,5-difluorophenyl)oxazol-4-yl)methylene)-2-methylpropane-2-sulfinamideHCID 178418306HCID 178418306, Verbindung

Produkt 1

HCID 67452308(+/-)-N-(1-(5-benzyl-2-(2,5-difluorophenyl)oxazol-4-yl)-2,2-dimethylpropyl)-2-methylpropane-2-sulfinamideAusbeute 38,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
-78 °C

Versuchsvorschrift

To a solution of (±)-N-((5-benzyl-2-(2,5-difluorophenyl)oxazol-4-yl)methylene)-2-methylpropane-2-sulfinamide (770 mg, 1.91 mmol) in anhydrous THF (7.6 mL) was slowly added tBuLi (1.7 M solution in pentane, 3.34 mL, 5.74 mmol) at −78° C. After the reaction mixture was stirred at −78° C. for 3 h, the reaction was quenched with MeOH (2 mL) followed by addition of saturated NH4Cl solution (10 mL). Upon warming up to room temperature, the reaction mixture was stirred for 30 min and then extracted with EtOAc (50 mL). The organic layer was washed with water and brine, dried over anhydrous Na2SO4, filtered, and concentrated. The crude product was purified by automatic column chromatography to yield (±)-N-(1-(5-benzyl-2-(2,5-difluorophenyl)oxazol-4-yl)-2,2-dimethylpropyl)-2-methylpropane-2-sulfinamide (340 mg, 38.6%) as a pale yellow solid. 1H NMR (CDCl3, 400 MHz): δ 7.64 (1H, m), 7.38-7.27 (4H, m), 7.27-7.21 (1H, m), 7.12-6.99 (2H, m), 4.24 (1H, m), 4.12 (2Hm), 3.92 (1H, m), 1.27 (9H, s), 0.95 (9H, s). LC/MS (uplc): MH+ 461.2, 1.34 min.

Aufarbeitung

  1. customat −78° C
  2. customthe reaction was quenched with MeOH (2 mL)
  3. additionfollowed by addition of saturated NH4Cl solution (10 mL)
  4. temperatureUpon warming up to room temperature
  5. stirringthe reaction mixture was stirred for 30 min
  6. extractionextracted with EtOAc (50 mL)
  7. washThe organic layer was washed with water and brine
  8. dry with materialdried over anhydrous Na2SO4
  9. filtrationfiltered
  10. concentrationconcentrated
  11. customThe crude product was purified by automatic column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-bf9f2b68a33c48ba9a50788abac496fb
Quelldatensatz
uspto-grants-2014_06
Patentnummer
US08748626B2

Notizen zur Reaktion

Wird geladen…