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

HRID 12416
ノート
印刷プレビュー

反応式

HRID 12416 の反応式
[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
参加物実験手順後処理出典と根拠反応ノート

参加物

7

反応物 4

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

生成物 1

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

試薬・触媒・溶媒

2
HCID 241Benzene溶媒HCID 8857Ethyl Acetate溶媒

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-f3dc3c9b14454ea5a9913cceb9841054
出典データセット
uspto-grants-2010_06
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07728005B2

反応ノート

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