Sodium Hydroxide → t-butyl (1S)-2-(3-methylphenoxy)-1-{[(3-nitrobenzyl)oxy]methyl}ethylcarbamate

HRID 12416

반응식

HRID 12416 반응식
[OH:1][CH2:2][C@H:3]([NH:13][C:14](=[O:20])[O:15][C:16]([CH3:19])([CH3:18])[CH3:17])[CH2:4][O:5][C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([CH3:12])[CH:7]=1.[N+:21]([C:24]1[CH:25]=[C:26]([CH:29]=[CH:30][CH:31]=1)[CH2:27]Br)([O-:23])=[O:22].S([O-])([O-])(=O)=O.C([N+](CCCC)(CCCC)CCCC)CCC.C([N+](CCCC)(CCCC)CCCC)CCC.[OH-].[Na+]>C(OCC)(=O)C.C1C=CC=CC=1>[CH3:12][C:8]1[CH:7]=[C:6]([CH:11]=[CH:10][CH:9]=1)[O:5][CH2:4][C@@H:3]([NH:13][C:14](=[O:20])[O:15][C:16]([CH3:17])([CH3:19])[CH3:18])[CH2:2][O:1][CH2:27][C:26]1[CH:29]=[CH:30][CH:31]=[C:24]([N+:21]([O-:23])=[O:22])[CH:25]=1

참가 물질

7

반응물 4

HCID 14798Sodium HydroxideHCID 77568Benzene, 1-(bromomethyl)-3-nitro-HCID 11433187Bis(tetrabutylammonium) sulphateHCID 68697680t-butyl (1S)-2-hydroxy-1-[(3-methylphenoxy)methyl]ethylcarbamate

생성물 1

HCID 86609359t-butyl (1S)-2-(3-methylphenoxy)-1-{[(3-nitrobenzyl)oxy]methyl}ethylcarbamate수율 76.6%

시약·촉매·용매 2

HCID 241Benzene용매HCID 8857Ethyl Acetate용매

실험 절차

To t-butyl (1S)-2-hydroxy-1-[(3-methylphenoxy)methyl]ethylcarbamate (300 mg) obtained in Step 1 of Example 118 were added 3-nitrobenzyl bromide (254 mg), tetrabutylammonium sulfate (91 mg), benzene (2.3 ml) and 50% aqueous sodium hydroxide solution (2.3 ml), and the mixture was stirred at room temperature for 1.5 hrs. The mixture was diluted with ethyl acetate and, after washing with water, the organic layer was dried over anhydrous sodium sulfate. The solvent was evaporated and the obtained crude product was purified by silica gel chromatography (ethyl acetate-hexane) to give the title compound (340 mg).

후처리

  1. washafter washing with water
  2. dry with materialthe organic layer was dried over anhydrous sodium sulfate
  3. customThe solvent was evaporated
  4. customthe obtained crude product
  5. customwas purified by silica gel chromatography (ethyl acetate-hexane)

출처 및 근거

ORD 기록
ord-f3dc3c9b14454ea5a9913cceb9841054
출처 데이터셋
uspto-grants-2010_06
특허 번호
US07728005B2

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