Preparation of Carbapenem Intermediate and Their Use

A process for the preparation of a compound of formula II:

• or a pharmaceutically acceptable salt thereof, wherein R is hydrogen or a protecting group and M is hydrogen or sodium ion;
• comprising:
• i) providing a compound of formula Ia:
• ii) converting the compound of formula Ia into the compound of formula II, wherein Ar is 2,4-dichlorophenyl, P is phosphor, and P′ is selected from the group consisting of allyl, 2,2,2,-trichloroethyl, 2-bromoethyl, benzhydryl, trityl, aryl, trimethysilyl, triethylsil, 4-methoxybenzyl, t-butyl, p-nitrobenzyl, hydrogen, and the like;
• and wherein the converting comprises the step of condensing the compound of formula Ia with a compound of formula V:
• to form a compound of formula VI:
• wherein P″ is selected from the group consisting of allyl, 2,2,2,-trichloroethyl, 2-bromoethyl, benzhydryl, trityl, aryl, trimethysilyl, triethylsil, 4-methoxybenzyl, t-butyl, p-nitrobenzyl, and the like.

A process for the preparation of a compound of Meropenem:

• comprising:
• i) providing a compound of formula Ia:
• ii) converting the compound of formula Ia into Meropenem, wherein Ar is 2,4-dichlorophenyl, P is phosphor, and P′ is selected from the group consisting of allyl, 2,2,2,-trichloroethyl, 2-bromoethyl, benzhydryl, trityl, aryl, trimethysilyl, triethylsil, 4-methoxybenzyl, t-butyl, p-nitrobenzyl, hydrogen, and the like;
• and wherein the converting comprises the step of condensing the compound of formula Ia with a compound of formula VII:
• to form a compound of formula VIII:
• wherein P″ is selected from the group consisting of allyl, 2,2,2,-trichloroethyl, 2-bromoethyl, benzhydryl, trityl, aryl, trimethysilyl, triethylsil, 4-methoxybenzyl, t-butyl, p-nitrobenzyl, and the like.

A process for the preparation of a compound of Doripenem:

• comprising:
• i) providing a compound of formula Ia:
• ii) converting the compound of formula Ia into Doripenem, wherein Ar is 2,4-dichlorophenyl, P is phosphor, and P′ is selected from the group consisting of allyl, 2,2,2,-trichloroethyl, 2-bromoethyl, benzhydryl, trityl, aryl, trimethysilyl, triethylsil, 4-methoxybenzyl, t-butyl, p-nitrobenzyl, hydrogen, and the like;
• and wherein the converting comprises the step of condensing the compound of formula Ia with a compound of formula IX:
• to form a compound of formula X:
• wherein P″ is selected from the group consisting of allyl, 2,2,2,-trichloroethyl, 2-bromoethyl, benzhydryl, trityl, aryl, trimethysilyl, triethylsil, 4-methoxybenzyl, t-butyl, p-nitrobenzyl, and the like.