Nitroxyl → 6-Aminopenicillanic acid

Participants

Reaction Conditions

Reaction Steps

To a suspension of 14.9 g of penicillin-G-potassium (= 40 mmols) in 60 ml of absolute methylene chloride 10 ml of N,N-dimethylaniline and 8.42 g (= 40 mmols) of methyl-n-octylphosphinic acid chloride were added successively while stirring. After an hour at 0°C the reaction mixture was cooled to -25°C and 9.0 g (= 43 mmols) of phosphorus pentachloride were introduced. After an hour at -25°C, 60 ml of n-butanol and 2 ml of N,N-dimethylaniline were introduced and by after-stirring for an hour at -25°C the iminoether was formed. Then, hydrolysis followed in the manner described in Example 1. 7.47 g (= 88.5 % of the theory) of 6-aminopenicillanic acid having a melting point of 195°C (decomposition) were isolated in the form of colorless crystals, the identity of which was examined in an analogous manner as described in Example 1.

Provenance & Evidence