RPR-202868

Chemical Name: 5-[(2S)-1,2,3,6-Tetrahydro-5-(4-morpholinylmethyl)-2-pyridinecarboxylic acid]pristinamycin IA ; N-(3-Hydroxypyridin-2-ylcarbonyl)-L-threonyl-D-(2-aminobutyryl)-L-prolyl-L-N-methyl-[4-(N,N-dimethylamino)]phenylalanyl-L-[5-(morpholin-4-ylmethyl)-1,2,3,6-tetrahydropyridin-2(S)-ylcarbonyl]-2-phenyl-L-glycine C-1.6-O-3.1-lactone
CAS No. 325965-23-9
项目整合开发状态: Preclinical
项目研究机构: Aventis Pharma (Originator)
合成路线:Reduction of the keto group of 5-delta-methylene pristinamycin IA (I) by means of NaBH4 in the presence of CeCl3 provided the allyl alcohol (II).Subsequent chlorination of (II) with SOCl2,furnished a mixture of compounds containing the 5-delta-(chloromethyl) (III) and the 5-gamma-chloro-5-delta-methylene (IV) derivatives.Treatment of the crude mixture with morpholine (V) in refluxing acetonitrile yielded the title 5-delta-morpholinomethyl analogue.

合成路线:In an alternative method,Michael addition of morpholine (V) to the unsaturated ketone (I) gave adduct (VI).Subsequent ketone reduction in (VI) with NaBH4 provided the corresponding alcohol (VII) as a diastereomeric mixture.Dehydration of alcohol (VII),upon treatment with diethylaminosulfur trifluoride,then yielded the title compound.