Diisopropylethylamine → HCID 21034893, Verbindung

To a stirred solution 3-amino-2-(3,4-dimethoxy-phenyl)-propionic acid ethyl ester hydrochloride (6.5 g, 25.8 mmol) and (3-sec-butoxy-phenyl)-acetic acid (5.9 g, 28.4 mmol) in N,N-dimethylformamide (130 mL) was added O-benzotriazole-N,N,N′,N′-tetramethyl-uronium hexaflurophosphate (HBTU) (11.8 g, 31.1 mmol) and diisopropylethylamine (14.8 mL, 85.0 mmol). The reaction mixture was stirred at room temperature for 15 hrs. The solvent was evaporated and the residue was diluted with ethyl acetate and saturated sodium bicarbonate solution. The aqueous phase was extracted with ethyl acetate (3×100 mL). The combined extracts were washed with 1N hydrogen chloride solution (50 mL), water (50 mL), saturated aqueous sodium chloride solution (50 mL), dried over anhydrous magnesium sulfate, filtered and concentrated in vacuo. Flash chromatography (Merck Silica gel 60, 70–230 mesh, 40% ethyl acetate/hexane, 100% ethyl acetate) afforded 3-[2-(3-sec-butoxy-phenyl)-acetylamino]-2-(3,4-dimethoxy-phenyl)-propionic acid ethyl ester (11.2 g, 98% yield) as a red oil.

1. customThe solvent was evaporated
2. additionthe residue was diluted with ethyl acetate and saturated sodium bicarbonate solution
3. extractionThe aqueous phase was extracted with ethyl acetate (3×100 mL)
4. washThe combined extracts were washed with 1N hydrogen chloride solution (50 mL), water (50 mL), saturated aqueous sodium chloride solution (50 mL)
5. dry with materialdried over anhydrous magnesium sulfate
6. filtrationfiltered
7. concentrationconcentrated in vacuo

ORD-Eintrag

ord-5c0ab5006974446ea9574d1fb2aa6926

Quelldatensatz

uspto-grants-2006_06

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US07067529B2