313653-10-0

Basic information

• Product Name: (3S,5R)-5-methyl-3-((4R,5S)-4-methyl-2-oxo-5-phenyloxazolidine-3-carbonyl)octanoic acid tert-butyl ester
• Synonyms: (3S,5R)-5-methyl-3-((4R,5S)-4-methyl-2-oxo-5-phenyloxazolidine-3-carbonyl)octanoic acid tert-butyl ester
• CAS NO: 313653-10-0
• Molecular Weight: 417.546
• Mol File: 313653-10-0.mol
• Article Data: 11

Chemical Properties

• CAS DataBase Reference: (3S,5R)-5-methyl-3-((4R,5S)-4-methyl-2-oxo-5-phenyloxazolidine-3-carbonyl)octanoic acid tert-butyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: (3S,5R)-5-methyl-3-((4R,5S)-4-methyl-2-oxo-5-phenyloxazolidine-3-carbonyl)octanoic acid tert-butyl ester(313653-10-0)
• EPA Substance Registry System: (3S,5R)-5-methyl-3-((4R,5S)-4-methyl-2-oxo-5-phenyloxazolidine-3-carbonyl)octanoic acid tert-butyl ester(313653-10-0)

Safety Data

• Hazardous Substances Data: 313653-10-0(Hazardous Substances Data)

Upstream product

• 5292-43-3 bromoacetic acid tert-butyl ester 
• 77943-39-6 4-methyl-5-phenyloxazolidin-2-one 
• 208836-20-8 (R)-2,6-Dimethyl-non-2-ene 
• 313653-16-6 methanesulfonic Acid (S)-3,7-dimethyl-oct-6-enyl Ester 
• 115109-01-8 (R)-4-methylheptanoic acid 
• 37577-28-9 (1S,2R)-(+)-norphedrine 
• 7540-51-4 (S)-3,7-dimethyl-6-octen-1-ol 
• 313653-09-7 (4R,5S)-4-methyl-3-((R)-4-methylheptanoyl)-5-phenyloxazolidin-2-one 
• 70-07-5 mephenoxalone 

Relevant articles and documents

Chemical development of an α2δ ligand, (3 S,5 R)-3-(Aminomethyl)-5-methyloctanoic acid

Three synthetic approaches, suitable for the large scale manufacture of the α2δ-ligand, (3S,5R)-3-(aminomethyl)-5-methyloctanoic acid 3, have been evaluated. The selected seven step manufacturing process has then been optimized and used to deliver over 20 kg of API; salient features of the synthesis include the use of 4,4,4-trimethoxybutyronitrile as an efficient four carbon amino acid equivalent. Highly selective kinetic resolution of the C3 stereocentre was accomplished via diastereoselective hydrolysis of a cyanoester intermediate using Amano Lipase PS-SD. Extensive process optimisation of the route starting from (R)-2-methylpentanol, led to significant improvements through telescoping, with less than 62 kg of solvent being needed to produce 1 kg of API.

METHODS FOR USING AMINO ACIDS WITH AFFINITY FOR THE ALPHA-2-DELTA PROTEIN

This invention relates to certain ?-amino acids that bind to the alpha-2-delta ((x2S) subunit of a calcium channel. These compounds and their pharmaceutically acceptable salts are useful in the treatment of a variety of psychiatric, pain and other disorders.

Combinations

The instant invention relates to a combination of an alpha-2-delta ligand and an AChE inhibitor for use in therapy, particularly in the treatment of pain, particularly neuropathic pain. Particularly preferred alpha-2-delta ligands are gabapentin and pregabalin. Particularly preferred ACHE inhibitors are donepezil (Aricept?), tacrine (cognex?), rivastigmine (Exelon?), physostgmine (Synapton?), galantamine (Reminyl), metrifonate (Promem), neostigmine (Prostigmin) and icopezil.