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

HRID 237874

Reaction equation

HRID 237874 reaction equation
[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

Participants

6

Reactant 3

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

Product 2

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

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

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).

Workup

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

Sources & evidence

ORD record
ord-f8444a373e3242a8b4fe1784f64676ed
Source dataset
uspto-grants-2014_02
Patent number
US08642603B2

Linked notes

Loading…