Hydrochloric Acid → HCID 69205592、化合物

HRID 30660ノート

反応式

HRID 30660 の反応式
[CH2:1]([O:8][C:9]([NH:11][C:12]1[CH:17]=[CH:16][C:15]([CH2:18][C:19]([O:21]CC)=O)=[CH:14][CH:13]=1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:24]([Mg]Br)[CH3:25].Cl.O1CC[CH2:31][CH2:30]1>>[CH2:30]([C:19]([OH:21])([CH2:24][CH3:25])[CH2:18][C:15]1[CH:14]=[CH:13][C:12]([NH:11][C:9](=[O:10])[O:8][CH2:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)=[CH:17][CH:16]=1)[CH3:31]

参加物

5

反応物 4

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 67375141HCID 67375141、化合物HCID 178418443HCID 178418443、化合物

生成物 1

HCID 69205592HCID 69205592、化合物

実験手順

To a mixture of ethyl (4-{[(benzyloxy)carbonyl]amino}phenyl)acetate (15.3 g) and tetrahydrofuran (100 mL) was added dropwise 1 M ethyl magnesium bromide (1 M tetrahydrofuran solution, 500 g) at 0° C. The reaction mixture was stirred at room temperature for 15 hrs. 1N Hydrochloric acid was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate and concentrated. The residue was subjected to silica gel column chromatography to give benzyl 4-(2-ethyl-2-hydroxybutyl)phenylcarbamate as colorless crystals from a fraction eluted with hexane-ethyl acetate (2:1-1:1, v/v). Recrystallization thereof from ethyl acetate-hexane gave colorless prism crystals (6.86 g, yield 43%). melting point: 99-100° C.

後処理

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe organic layer was washed with saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated

出典と根拠

ORDレコード
ord-265febaad9564ec5b597293b802dd073
出典データセット
uspto-grants-2008_09
特許番号
US07423159B2

反応ノート

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