Sodium Iodide → [4-(4-Benzyloxycarbonylaminobutyl)phenoxy]acetic acid ethyl ester

A solution of [4-(4-hydroxyphenyl)butyl]carbamic acid benzyl ester (2.0 g, 6.7 mmol), potassium carbonate (1.0 g, 7.3 mmol), sodium iodide (0.4 g, 2.7 mmol), and DMF (10 mL) was stirred for 30 minutes. A solution of ethyl bromoacetate (0.8 mL, 7.4 mmol) in DMF (10 mL) was added dropwise to the reaction. The reaction was further stirred at room temperature for 3 days, and then poured into water (200 mL). The product was extracted with ethyl acetate. The organic layer was dried over sodium sulfate and concentrated in vacuo. The residue was purified by flash chromatography (silica gel, 1:5 ethyl acetate/hexanes, v/v) to provide the desired product 480 (2.3 g, 89%) as a white solid. 1H NMR (300 MHz, CDCl3) δ 1.34 (t, 3H), 1.57 (m, 4H), 2.56 (t, 2H), 3.20 (q, 2H), 4.25 (q, 2H), 4.59 (s, 2H), 5.10 (s, 2H), 6.85 (d, 2H), 7.06 (d, 2H), 7.38 (m, 5H).

1. extractionThe product was extracted with ethyl acetate
2. dry with materialThe organic layer was dried over sodium sulfate
3. concentrationconcentrated in vacuo
4. customThe residue was purified by flash chromatography (silica gel, 1:5 ethyl acetate/hexanes

ORD-Eintrag

ord-ca37933af49d49cba7a93533a2393aa2

Quelldatensatz

uspto-grants-2011_01

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US07875619B2