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

HRID 237875ノート

反応式

HRID 237875 の反応式
[CH:1]1([C:7]2[CH:26]=[CH:25][C:10]([O:11][CH2:12][CH:13]3[O:24][C:16]4=[N:17][C:18](=[O:23])[C:19]([S:21][CH3:22])=[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:28]1.O.O.O.O.[Na+].[OH-].[Na+]>CC(O)=O>[CH:1]1([C:7]2[CH:26]=[CH:25][C:10]([O:11][CH2:12][C@H:13]3[O:24][C:16]4=[N:17][C:18](=[O:23])[C:19]([S:21]([CH3:22])=[O:28])=[CH:20][N:15]4[CH2:14]3)=[CH:9][CH:8]=2)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

参加物

5

反応物 3

HCID 14798Sodium HydroxideHCID 23693097Sodium;3-oxidodioxaborirane;tetrahydrateHCID 685274682-(4-Cyclohexyl-phenoxymethyl)-6-methylsulfanyl-2,3-dihydro-oxazolo[3,2-a]pyrimidin-7-one

生成物 1

HCID 59252524(S)-2-(4-cyclohexyl-phenoxymethyl)-6-methanesulfinyl-2,3-dihydro-oxazolo[3,2-a]pyrimidin-7-one収率 3.7%

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-methylsulfanyl-2,3-dihydro-oxazolo[3,2-a]pyrimidin-7-one (0.284 g, 0.763 mmol), prepared in accordance with the procedures set forth in Example 98, in HOAc (6 mL) was added sodium perborate tetrahydrate (0.313 g, 2.04 mmol). The reaction mixture was stirred at room temperature overnight. The reaction mixture was then neutralized with NaOH (2N) to PH˜9 after which it was extracted with EtOAc three times. The organic phase was washed with brine and dried (Na2SO4). Silica gel chromatography (0-8% EtOH/CH2Cl2) provided 0.03 g of (S)-2-(4-cyclohexyl-phenoxymethyl)-6-methanesulfonyl-2,3-dihydro-oxazolo[3,2a]pyrimidin-7-one, 0.042 g of (S)-2-(4-cyclohexyl-phenoxymethyl)-6-methanesulfinyl-2,3-dihydro-oxazolo[3,2-a]pyrimidin-7-one (Diastereomer 1) and 0.011 g of (S)-2-(4-cyclohexyl-phenoxymethyl)-6-methanesulfinyl-2,3-dihydro-oxazolo[3,2-a]pyrimidin-7-one (Diastereomer 2).

後処理

  1. extractionwas 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-e6f093d3dd2243a091a038a5189fb767
出典データセット
uspto-grants-2014_02
特許番号
US08642603B2

反応ノート

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