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

HRID 237874

반응식

HRID 237874 반응식
[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

참가 물질

6

반응물 3

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

생성물 2

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

시약·촉매·용매 1

HCID 176Acetic Acid용매

실험 절차

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).

후처리

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

출처 및 근거

ORD 기록
ord-f8444a373e3242a8b4fe1784f64676ed
출처 데이터셋
uspto-grants-2014_02
특허 번호
US08642603B2

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