Acetylphenylalanine methyl ester → N-acetylphenylalanine aldehyde

HRID 1765978

Reaction equation

HRID 1765978 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) is dissolved in ethylene glycol dimethyl ether. The solution is cooled to −70° C. and diisobutylaluminum hydride (25.3 mL of a 1.5M solution in toluene, 39 mmol) is added. The resulting reaction mixture is stirred at −70° C. for 2 hours. The reaction is quenched by addition of 2N hydrochloric acid. The mixture is extracted 4 times with cold ethyl acetate and 4 times with toluene. The extracts are combined, washed with brine and dried over magnesium sulfate. Concentration in vacuo followed by silica gel chromatography furnishes 2.7 g of a white solid. The NMR is as reported in the literature, Biochemistry, 18: 921–926 (1979).

Workup

  1. customThe resulting reaction mixture
  2. customThe reaction is quenched by addition of 2N hydrochloric acid
  3. extractionThe mixture is 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-3001f6fc68ae4e40886a841775f238e4
Source dataset
uspto-grants-2007_06
Patent number
US07229966B2

Linked notes

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