Réaction #709603

Équation de réaction

diisopropylethylamine

diphenylphosphoryl chloride

p-nitrobenzyl (5R,6S)-6-[(1R)-1-hydroxyethyl]-2-oxo-1-carbapenam-3-carboxylate

diisopropylethylamine

2-(3-methoxyiminopyrrolidin-1-yl)-2-iminoethylmercaptan hydrochloride

→

title compound

Rendement 5.8%

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

Rendement 5.8%

Solvants

tetrahydrofuran

water

phosphate

acetonitrile

dimethylsulfoxide

ether

Conditions de réaction

Traitement

1. 1
   Températurecooling
2. 2
   workup.STIRRINGthe mixture was stirred for a further 20 minutes with ice-
3. 3
   Températurecooling
4. 4
   Autrethe solvent was decanted off from the gummy material which
5. 5
   Autreformed
6. 6
   Autrepurified in the same manner as in Example 2

Mode opératoire

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 mixture was stirred for one hour with ice-cooling. A solution of 0.18 ml of diisopropylethylamine and 307 mg of 2-(3-methoxyiminopyrrolidin-1-yl)-2-iminoethylmercaptan hydrochloride in 3 ml of dimethylsulfoxide was then added dropwise, and the mixture was 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 subjected to catalytic hydrogenation 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 23 mg of the title compound.

Source