Sodium Thiosulfate → 4-[N-dodecyl-N-[2-[4-(3oxo-4,4,4-trifluorobut-1-yl)phenoxy]ethyl]amino]butanoic acid, ethyl ester

Temperature

22 °C

A suspension of 1,1, 1-triacetoxy-1,1-dihydro-1,2-benziodoxol-3(1H)-one (Dess-Martin periodinane, 1.7 g, 4.0 mmol) in dichloromethane (20 ml) was treated with 4-[N-dodecyl-N-2-[4-[4,4,4-trifluoro-3-hydroxybutyl]phenoxy]ethylamino]butanoic acid, ethyl ester (430 mg, 0.79 mmol) dissolved in dichloromethane (5 ml). The mixture was stirred at 22° C. for 4 h, poured into a saturated aqueous sodium bicarbonate and sodium thiosulfate (100 ml) and extracted with ethyl acetate (2×100 ml). The combined oganic layers were washed with sat. sodium bicarbonate (2×60 ml), brine (60 ml), dried over sodium sulfate and concentrated in vacuo . The residue was chromatographed on silica gel (hexane/ethyl acetate 2:1 to 1.5:1) to afford the title compound (333 mg, 77%) as a colorless oil.

1. extractionextracted with ethyl acetate (2×100 ml)
2. washThe combined oganic layers were washed with sat. sodium bicarbonate (2×60 ml), brine (60 ml)
3. dry with materialdried over sodium sulfate
4. concentrationconcentrated in vacuo
5. customThe residue was chromatographed on silica gel (hexane/ethyl acetate 2:1 to 1.5:1)

ORD record

ord-50bf09b9f811460a83d29492724c96ce

Source dataset

uspto-grants-2002_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06350892B1