Acetylphenylalanine methyl ester → N-acetylphenylalanine aldehyde

HRID 891836

反応式

HRID 891836 の反応式
C[O:2][C:3](=O)[C@H:4]([CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)[NH:5][C:6](=[O:8])[CH3:7].[H-].C([Al+]CC(C)C)C(C)C>COCCOC.C1(C)C=CC=CC=1>[C:6]([NH:5][C@H:4]([CH:3]=[O:2])[CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)(=[O:8])[CH3:7]

参加物

5

反応物 2

HCID 704002Acetylphenylalanine methyl esterHCID 21225700Diisobutylaluminumhydride

生成物 1

HCID 193217N-acetylphenylalanine aldehyde収率 74.3%

試薬・触媒・溶媒 2

HCID 1140Toluene溶媒HCID 80711,2-Dimethoxyethane溶媒

反応条件

温度
-70 °C

実験手順

N-Acetylphenylalanine methyl ester (4.2 g, 19 mmol) was dissolved in ethylene glycol dimethyl ether. The solution was cooled to −70° C. and diisobutylaluminum hydride (25.3 mL of a 1.5M solution in toluene, 39 mmol) was added. The resulting reaction mixture was stirred at −70° C. for 2 hours. The reaction was quenched by addition of 2N hydrochloric acid. The mixture was extracted 4 times with cold ethyl acetate and 4 times with toluene. The extracts were combined, washed with brine and dried over magnesium sulfate. Concentration in vacuo followed by silica gel chromatography furnished 2.7 g of a white solid. The NMR was identical to that reported in the literature, Biochemistry, 1979, 18, 921–926.

後処理

  1. customThe resulting reaction mixture
  2. customThe reaction was quenched by addition of 2N hydrochloric acid
  3. extractionThe mixture was extracted 4 times with cold ethyl acetate and 4 times with toluene
  4. washwashed with brine
  5. dry with materialdried over magnesium sulfate
  6. concentrationConcentration in vacuo

出典と根拠

ORDレコード
ord-59c12a8cd0714f2ab4e058538fac91b4
出典データセット
uspto-grants-2006_02
特許番号
US07005141B2

関連ノート

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