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 1046060

Reaktionsgleichung

Reaktionsgleichung von HRID 1046060
[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-408a8fa337ae42d59379c1c296bcf6ba
Quelldatensatz
uspto-grants-2013_10
Patentnummer
US08569292B2

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