Diphenylphosphinic chloride → (5R,6S)-2-[2-(3-Hydroxyiminopyrrolidin-1-yl)-2-iminoethylthio]-6-[(1R)-1-hydroxyethyl]-1-carbapen-2-em-3-carboxylic acid

0.21 ml of diisopropylethylamine and 0.22 ml of diphenylphosphoryl chloride were added dropwise to an ice-cooled solution of 363 mg of p-nitrobenzyl (5R,6S)-6-[(1R)-1-hydroxyethyl]-2-oxo-1-carbapenam-3-carboxylate in 5 ml of anhydrous acetonitrile, and the solution was stirred for one hour with ice-cooling. A solution of 0.18 ml of diisopropylethylamine and 282 mg of 2-(3-hydroxyiminopyrrolidin-1-yl)-2-iminoethylmercaptan hydrochloride in 3 ml of dimethylsulfoxide was added, and the mixture was then stirred for a further 20 minutes with ice-cooling. The reaction mixture was poured into 100 ml of anhydrous ether, and the solvent was decanted off from the gummy material which formed. This material was dissolved in a mixture of 20 ml of tetrahydrofuran, 7 ml of water and 23 ml of 0.1M phosphate buffer (pH 7.0), and the solution was catalytically hydrogenated at room temperature for 2 hours in the presence of 0.3 g of 10 % palladium-carbon. The product was worked up and purified in the same manner as in Example 2, giving 15 mg of the title compound.

1. temperaturecooling
2. stirringthe mixture was then stirred for a further 20 minutes with ice-
3. temperaturecooling
4. customthe solvent was decanted off from the gummy material which
5. customformed
6. custompurified in the same manner as in Example 2

ORD record

ord-51573398b3274c11a4f269dea7fd9a71

Source dataset

uspto-grants-1988_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04771046