1,2-Dichloroethane → 2-tert-butoxycarbonylamino-5-((S)-2-methoxymethyl-pyrrolidin-1-yl)-5-oxo-pentanoic acid methyl ester

To a mixture of 4-(tert-butoxycarbonylamino)-5-methoxy-5-oxopentanoic acid (1.05 g, 4 mmol), (S)-2-(methoxymethyl)-pyrrolidine (0.46 g, 4 mmol), and 1-hydroxybenzotriazole hydrate (HOBt hydrate, 0.54 g, 4 mmol) in CH2Cl2 (10 mL) was added EDC (0.77 g, 4 mmol). The reaction mixture was stirred at ambient temperature for 12 h, diluted with CH2Cl2 (40 mL), washed sequentially with saturated aqueous sodium bicarbonate (20 mL), 0.5 N aqueous citric acid (20 mL) and brine (20 mL), dried over magnesium sulfate, filtered, and concentrated under reduced pressure to yield a crude viscous oil. The crude oil was purified by flash chromatography (silica gel, 50% ethyl acetate/hexanes) to give the title compound (1.36 g, 95%) as a colorless oil.

1. washwashed sequentially with saturated aqueous sodium bicarbonate (20 mL), 0.5 N aqueous citric acid (20 mL) and brine (20 mL)
2. dry with materialdried over magnesium sulfate
3. filtrationfiltered
4. concentrationconcentrated under reduced pressure
5. customto yield a crude viscous oil
6. customThe crude oil was purified by flash chromatography (silica gel, 50% ethyl acetate/hexanes)

ORD-Eintrag

ord-d06644afaa0d4da1bc59b9ca277d7bce

Quelldatensatz

uspto-grants-2011_09

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US08022096B2