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-ac1bec00777d4bffbef2b3de68f8cc3d

Quelldatensatz

uspto-grants-1998_08

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US05792451