Simultaneous Hydrogenolysis of p-Nitrobenzyl Esters and Carbamates Side-Chains in the THF 1β-Carbapenem OCA-983 in Biphasic Media

Title: Simultaneous Hydrogenolysis of p-Nitrobenzyl Esters and Carbamates Side-Chains in the THF 1β-Carbapenem OCA-983 in Biphasic Media

Volume: 2 Issue: 1

Author(s): Zhong Li, David How, Phaik-Eng Sum, Yang-I Lin and Tarek S. Mansour

Affiliation:

Keywords: ethyl acetate-H2O, n-butanol-H2O, biphasic media, PNB/PNZ side-chains, deprotection, carbapenems, OCA-983

Abstract: Deprotection of p-nitrobenzyl esters and valyl carbamates in carbapenem CL 192,276 produced the active compound OCA-983 in excellent yields. Straight chain alkanols such as 1-butanol, 1-pentanol and 1-hexanol in water at certain ratios were effective solvent systems. Alkyl acetates in water also resulted in simultaneous deprotection of PNB and PNZ side-chains albeit at slower rates. The deprotected carbapenem was isolated in excellent yield and purity after removal of the aqueous media. This procedure is applicable to sensitive compounds that are soluable in water without the need to use a buffer and allows for ease of isolation from the aqueous phase.

Cite this article as:

Li Zhong, How David, Sum Phaik-Eng, Lin Yang-I and Mansour S. Tarek, Simultaneous Hydrogenolysis of p-Nitrobenzyl Esters and Carbamates Side-Chains in the THF 1β-Carbapenem OCA-983 in Biphasic Media, Medicinal Chemistry 2006; 2 (1) . https://dx.doi.org/10.2174/157340606775197741