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

HRID 237874

反応式

HRID 237874 の反応式
[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

参加物

6

反応物 3

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

生成物 2

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

試薬・触媒・溶媒 1

HCID 176Acetic Acid溶媒

実験手順

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).

後処理

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

出典と根拠

ORDレコード
ord-f8444a373e3242a8b4fe1784f64676ed
出典データセット
uspto-grants-2014_02
特許番号
US08642603B2

関連ノート

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