Acetylphenylalanine methyl ester → N-acetylphenylalanine aldehyde

HRID 891836노트

반응식

HRID 891836 반응식
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]

참가 물질

5

반응물 2

HCID 704002Acetylphenylalanine methyl esterHCID 21225700Diisobutylaluminumhydride

생성물 1

HCID 193217N-acetylphenylalanine aldehyde수율 74.3%

시약·촉매·용매 2

HCID 1140Toluene용매HCID 80711,2-Dimethoxyethane용매

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온도
-70 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-59c12a8cd0714f2ab4e058538fac91b4
출처 데이터셋
uspto-grants-2006_02
특허 번호
US07005141B2

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