Reaktion #4216

Reaktionsgleichung

(2S-trans)[1-[[2-[3-[[(1,1-Dimethylethoxy)-carbonyl]amino]-2-oxo-1-imidazolidinyl]-2-oxoethoxy]hydroxyphosphinyl]-2-methyl-4-oxo-3-azetidinyl]carbamic acid, phenylmethyl ester

monopotassium

anisole

trifluoroacetic acid

sodium bicarbonate

→

title compound

(2S-trans)[1-[[2-(3-Amino-2-oxo-1-imidazolidinyl)-2-oxoethoxy]hydroxyphosphinyl]-2-methyl-4-oxo-3-azetidinyl]carbamic acid, phenylmethyl ester

Lösungsmittel

water

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeThe solution was evaporated in vacuo at ambient temperature
2. 2
   SonstigeThe residue was triturated with hexane (50 ml) and diethyl ester (2×50 ml)
3. 3
   Sonstigeto give a white solid
4. 4
   SonstigeThis solution was chromatographed on a column of CHP20P reverse phase resin
5. 5
   Wascheneluted with an acetonitrile/water gradient
6. 6
   Sonstigeevaporated in vacuo to ~100 ml

Vorschrift

(2S-trans)[1-[[2-[3-[[(1,1-Dimethylethoxy)-carbonyl]amino]-2-oxo-1-imidazolidinyl]-2-oxoethoxy]hydroxyphosphinyl]-2-methyl-4-oxo-3-azetidinyl]carbamic acid, phenylmethyl ester, monopotassium salt (5.9 g, 10 mmol) was treated at 0° C. sequentially with anisole (25 ml) and trifluoroacetic acid (60 ml), and the solution was stirred for six hours. The solution was evaporated in vacuo at ambient temperature and then co-evaporated with toluene (10 ml). The residue was triturated with hexane (50 ml) and diethyl ester (2×50 ml) to give a white solid. The solid was dissolved in water (10 ml) and the pH adjusted to 2.5 with sodium bicarbonate. This solution was chromatographed on a column of CHP20P reverse phase resin and eluted with an acetonitrile/water gradient. The appropriate fractions were combined and evaporated in vacuo to ~100 ml. This was lyophilized to give the title compound as a white solid, 2.520 g.

Quelle