Sodium Hydroxide → (S)-6-benzenesulfinyl-2-(4-cyclohexyl-phenoxymethyl)-2,3-dihydro-oxazolo[32-a]pyrimidin-7-one

HRID 237874

Reaktionsgleichung

Reaktionsgleichung von HRID 237874
[CH:1]1([C:7]2[CH:31]=[CH:30][C:10]([O:11][CH2:12][CH:13]3[O:29][C:16]4=[N:17][C:18](=[O:28])[C:19]([S:21][C:22]5[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=5)=[CH:20][N:15]4[CH2:14]3)=[CH:9][CH:8]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.B1([O-])O[O:33]1.[OH2:36].[OH2:37].O.O.[Na+].[OH-].[Na+]>CC(O)=O>[C:22]1([S:21]([C:19]2[C:18](=[O:28])[N:17]=[C:16]3[O:29][C@H:13]([CH2:12][O:11][C:10]4[CH:30]=[CH:31][C:7]([CH:1]5[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]5)=[CH:8][CH:9]=4)[CH2:14][N:15]3[CH:20]=2)(=[O:37])=[O:36])[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.[C:22]1([S:21]([C:19]2[C:18](=[O:28])[N:17]=[C:16]3[O:29][C@H:13]([CH2:12][O:11][C:10]4[CH:30]=[CH:31][C:7]([CH:1]5[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]5)=[CH:8][CH:9]=4)[CH2:14][N:15]3[CH:20]=2)=[O:33])[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

Komponenten

6

Edukt 3

HCID 14798Sodium HydroxideHCID 23693097Sodium;3-oxidodioxaborirane;tetrahydrateHCID 685292682-(4-Cyclohexyl-phenoxymethyl)-6-phenylsulfanyl-2,3-dihydro-oxazolo[3,2-a]pyrimidin-7-one

Produkt 2

HCID 59252504(S)-6-benzenesulfinyl-2-(4-cyclohexyl-phenoxymethyl)-2,3-dihydro-oxazolo[32-a]pyrimidin-7-oneHCID 59252521HCID 59252521, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 176Acetic AcidLösungsmittel

Versuchsvorschrift

To a solution of 2-(4-cyclohexyl-phenoxymethyl)-6-phenylsulfanyl-2,3-dihydro-oxazolo[3,2-a]pyrimidin-7-one (0.313 g, 0.675 mmol) (prepared in accordance with the procedures set forth in Example 93), in HOAc (6 mL) was added sodium perborate tetrahydrate (0.277 g, 1.80 mmol). The reaction mixture was stirred at room temperature overnight. The reaction mixture was then neutralized with NaOH (2N) to PH˜9. The mixture was extracted with EtOAc three times. The organic phase was washed with brine and dried (Na2SO4). Silica gel chromatography (0-6% 2-propanol/CH2Cl2) provided 0.026 g of (S)-6-benzenesulfonyl-2-(4-cyclohexyl-phenoxymethyl)-2,3-dihydro-oxazolo[3,2-a]pyrimidin-7-one, 0.022 g of (S)-6-benzenesulfinyl-2-(4-cyclohexyl-phenoxymethyl)-2,3-dihydro-oxazolo[32-a]pyrimidin-7-one (Diastereomer 1) and 0.086 g of (S)-6-benzenesulfinyl-2-(4-cyclohexyl-phenoxymethyl)-2,3-dihydro-oxazolo[32-a]pyrimidin-7-one (diastereomer 2).

Aufarbeitung

  1. extractionThe mixture was extracted with EtOAc three times
  2. washThe organic phase was washed with brine
  3. dry with materialdried (Na2SO4)

Quellen und Nachweise

ORD-Eintrag
ord-f8444a373e3242a8b4fe1784f64676ed
Quelldatensatz
uspto-grants-2014_02
Patentnummer
US08642603B2

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