Potassium Carbonate → (S)-3-((S)-1-(4-bromophenyl)ethyl)-6-(2-(1,1-dioxo-isothiazolidin-2-yl)ethyl)-6-phenyl-1,3-oxazinan-2-one

HRID 1191734

Reaktionsgleichung

Reaktionsgleichung von HRID 1191734
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C@@H:8]([N:10]2[CH2:15][CH2:14][C@@:13]([CH2:22][CH2:23]CS([O-])(=O)=O)([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[O:12][C:11]2=[O:29])[CH3:9])=[CH:4][CH:3]=1.C([O-])([O-])=O.[K+].[K+].[S:36]1(=[O:42])(=[O:41])[CH2:40][CH2:39][CH2:38][NH:37]1>C(#N)C>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C@@H:8]([N:10]2[CH2:15][CH2:14][C@:13]([CH2:22][CH2:23][N:37]3[CH2:38][CH2:39][CH2:40][S:36]3(=[O:42])=[O:41])([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[O:12][C:11]2=[O:29])[CH3:9])=[CH:4][CH:3]=1

Komponenten

5

Edukt 3

HCID 11430Potassium CarbonateHCID 6421571,3-PropanesultamHCID 86649411HCID 86649411, Verbindung

Produkt 1

HCID 59635736(S)-3-((S)-1-(4-bromophenyl)ethyl)-6-(2-(1,1-dioxo-isothiazolidin-2-yl)ethyl)-6-phenyl-1,3-oxazinan-2-oneAusbeute 1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

To a solution of 2-((S)-3-((S)-1-(4-bromophenyl)ethyl)-2-oxo-6-phenyl-1,3-oxazinan-6-yl)ethyl-methanesulfonate (360 mg, 0.75 mmol) and K2CO3 (207 mg, 1.5 mmol) in acetonitrile (10 mL) was added isothiazolidine 1,1-dioxide (121 mg, 4.6 mmol), and the mixture was refluxed overnight. The mixture was filtered and the filtrate was concentrated to give the crude product, which was purified by preparative HPLC to afford compound (S)-3-((S)-1-(4-bromophenyl)ethyl)-6-(2-(1,1-dioxo-isothiazolidin-2-yl)ethyl)-6-phenyl-1,3-oxazinan-2-one (2.43 mg, 1%). LC-MS Method 2 tR=1.37 min, m/z=509, 507. 1H NMR (CDCl3): 1.48 (t, 3H), 2.05-2.41 (m, 7H), 2.71-2.92 (m, 2H), 3.11 (m, 3H), 3.21 (m, 2H), 5.58 (m, 1H), 6.73 (d, 2H), 7.18 (m, 1H), 7.23 (m, 3H); 7.35 (m, 3H).

Aufarbeitung

  1. temperaturethe mixture was refluxed overnight
  2. filtrationThe mixture was filtered
  3. concentrationthe filtrate was concentrated
  4. customto give the crude product, which
  5. customwas purified by preparative HPLC

Quellen und Nachweise

ORD-Eintrag
ord-9ebe7f3c9ca74469bfc5c285acf84fb6
Quelldatensatz
uspto-grants-2014_03
Patentnummer
US08680093B2

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