Acetylphenylalanine methyl ester → N-acetylphenylalanine aldehyde

Temperatur

-70 °C

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.

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

ORD-Eintrag

ord-59c12a8cd0714f2ab4e058538fac91b4

Quelldatensatz

uspto-grants-2006_02

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US07005141B2