Ethyl 4-oxobutanoate → 4-[N-dodecyl-N-2-[4-iodophenoxy]ethylamino]butanoic acid, ethyl ester

Temperatur

22 °C

To a mixture of N-2-[4-iodophenoxy]ethyldodecylamine ( 4.0 g, 9.3 mmol) and sodium cyanoborohydride (1.45 g, 23 mmol) in methanol (80 ml) was added dropwise a solution of ethyl 4-oxobutyrate (Fournet, G. ; Balme, G.; Barieux, J. J. and Gore, J. Tetrahedron, 1988, 44, 5821) (2.4 g, 18 mmol) in methanol (20 ml) over a period of 10 min. The resulting mixture was stirred at 22° C. for 24 h, and then diluted with ethyl acetate (600 ml), washed with brine (3×250 ml). The aqueous phase was extracted with ethyl acetate (150 ml), and the combined organic layers were dried over sodium sulfate and concentrated in vacuo. The residue was chromatographed on silica gel (Hexane/ethyl acetate 8:1 to 6:1) to afford the title compound (4.5 g, 89%) as a colorless oil.

1. washwashed with brine (3×250 ml)
2. extractionThe aqueous phase was extracted with ethyl acetate (150 ml)
3. dry with materialthe combined organic layers were dried over sodium sulfate
4. concentrationconcentrated in vacuo
5. customThe residue was chromatographed on silica gel (Hexane/ethyl acetate 8:1 to 6:1)

ORD-Eintrag

ord-e5fea5b26ca14b5caae909f62ed46e01

Quelldatensatz

uspto-grants-2001_07

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US06255496B1