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

HRID 237875노트

반응식

HRID 237875 반응식
[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

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 176Acetic Acid용매

실험 절차

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).

후처리

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

출처 및 근거

ORD 기록
ord-e6f093d3dd2243a091a038a5189fb767
출처 데이터셋
uspto-grants-2014_02
특허 번호
US08642603B2

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