Acetylphenylalanine methyl ester → N-acetylphenylalanine aldehyde

HRID 891836

Reaction equation

HRID 891836 reaction equation
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]

Participants

5

Reactant 2

HCID 704002Acetylphenylalanine methyl esterHCID 21225700Diisobutylaluminumhydride

Product 1

HCID 193217N-acetylphenylalanine aldehydeYield 74.3%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 80711,2-DimethoxyethaneSolvent

Conditions

Temperature
-70 °C

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-59c12a8cd0714f2ab4e058538fac91b4
Source dataset
uspto-grants-2006_02
Patent number
US07005141B2

Linked notes

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