Sodium Carbonate → (S)-2-(4-Cyclohexyl-phenoxymethyl)-5-phenylsulfanylmethyl-2,3-dihydro-oxazolo[3,2-a]pyrimidin-7-one

HRID 237876

Reaktionsgleichung

Reaktionsgleichung von HRID 237876
[C:1]1([S:7]([CH2:10][C:11]2[N:16]3[CH2:17][C@@H:18]([CH2:20][O:21][C:22]4[CH:27]=[CH:26][C:25]([CH:28]5[CH2:33][CH2:32][CH2:31][CH2:30][CH2:29]5)=[CH:24][CH:23]=4)[O:19][C:15]3=[N:14][C:13](=[O:34])[CH:12]=2)(=O)=O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.B1([O-])OO1.O.O.O.O.[Na+].[OH-].[Na+].C([O-])([O-])=O.[Na+].[Na+]>CC(O)=O>[CH:28]1([C:25]2[CH:26]=[CH:27][C:22]([O:21][CH2:20][C@H:18]3[O:19][C:15]4=[N:14][C:13](=[O:34])[CH:12]=[C:11]([CH2:10][S:7][C:1]5[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=5)[N:16]4[CH2:17]3)=[CH:23][CH:24]=2)[CH2:33][CH2:32][CH2:31][CH2:30][CH2:29]1

Komponenten

6

Edukt 4

HCID 10340Sodium CarbonateHCID 14798Sodium HydroxideHCID 23693097Sodium;3-oxidodioxaborirane;tetrahydrateHCID 25072999HCID 25072999, Verbindung

Produkt 1

HCID 59252530(S)-2-(4-Cyclohexyl-phenoxymethyl)-5-phenylsulfanylmethyl-2,3-dihydro-oxazolo[3,2-a]pyrimidin-7-oneAusbeute 85,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 176Acetic AcidLösungsmittel

Versuchsvorschrift

To a solution of (S)-5-benzenesulfonylmethyl-2-(4-cyclohexyl-phenoxymethyl) -2,3-dihydro-oxazolo[3,2-a]pyrimidin-7-one (0.5 g, 1.11 mmol), prepared in accordance with the procedures described in Step 1 and 2 of Example 120, in HOAc (20 mL) was added sodium perborate tetrahydrate (0.446 g, 2.90 mmol). The reaction mixture was stirred at room temperature for 9 hours. The reaction mixture was neutralized with NaOH (2N) to pH˜7 and further to pH˜10 with Na2CO3. The mixture was extracted with EtOAc three times. The organic phase was washed with brine and dried (Na2SO4). Silica gel chromatography (2-8% methanol/CH2Cl2) provided 0.425 g of (S)-2-(4-cyclohexyl-phenoxymethyl)-5-phenylsulfanylmethyl-2,3-dihydro-oxazolo[3,2-a]pyrimidin-7-one. [α]D25 −3.80 (c 0.5, CHCl3).

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-6f2bd4d13300459e8674a169afebb3d9
Quelldatensatz
uspto-grants-2014_02
Patentnummer
US08642603B2

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