197847-12-4

Upstream product

• 3282-30-2 pivaloyl chloride 

Downstream Products

• 223595-23-1 5-bromo-2-{(1R)-1-[(2,2-dimethylpropanoyl)amino]ethyl}benzyl chloride 
• 223595-22-0 5-bromo-2-{(1R)-1-[(2,2-dimethylpropanoyl)amino]ethyl}benzyl acetate 

Relevant academic research and scientific papers

Chiral recognition in the solid state: Crystallographically characterized diastereomeric co-crystals between a synthetic chiral selector (Whelk-O1) and a representative chiral analyte

Designed to distinguish between the enantiomers of compounds possessing commonly occurring structural features, the chiral selector used in the chiral stationary phase (CSP) 1 (Whelk-O1) is broadly applicable. In an effort to further the understanding of the mechanism of chiral recognition with this chiral selector, both diastereomeric combinations of selector 1 and a representative analyte, the pivalamide of p-bromo-α-phenylethylamine, 2, were successfully co-crystallized and characterized by single crystal X-ray diffraction. The crystal corresponding to the complex that is more stable in solution is consistent with our previously reported chiral recognition model. The aromatic portion of 2 is in the cleft of selector 1, displaying both face-to-face and face-to-edge π-π interactions as well as a hydrogen bond between the benzamide proton of the selector and the carbonyl oxygen of the analyte. For the crystal corresponding to the complex, which is less stable in solution, the aromatic portion of 2 is not in the cleft of selector 1, having approached from the opposite face of the π-acidic dinitrobenzamide moiety so as to undergo face-to-face π-π and hydrogen bonding interactions. Comparisons of these structures and their relevance to enantioselective chromatography are also discussed.

Investigation of a broadly applicable chiral selector used in enantioselective chromatography (Whelk-O 1) as a chiral solvating agent for NMR determination of enantiomeric composition

A chiral solvating agent (CSA) based on the chiral selector used in the Whelk-O 1 chiral stationary phase (CSP) was prepared and its scope evaluated. This chiral selector possesses a cleft flanked with aromatic groups and produces upfield chemical shifts for analytes, which are held in this cleft. The enantiomers of each of the Whelk-O 1 resolvable analytes surveyed show non-equivalent 1H NMR spectra at room temperature with the addition of only 0.5 equiv of the CSA. Similar non-equivalence is sometimes noted for enantiomers, which do not resolve on this CSP. In such cases, it is apparent that a hydrogen bond acceptor is required and higher CSA to substrate ratios and/or lower temperatures may be needed if adequate resolution of enantiomeric signals is to be obtained.

Processes for producing 7-isoindolinequinolonecarboxylic derivatives and intermediates therefor, salts of 7-isoindolinequinolonecarboxylic acids, hydrates thereof, and composition containing the same as active ingredient

This invention relates to processes for producing a 7-isoindoline-quinolonecarboxylic acid derivative represented by the general formula [1] which is useful as an antibacterial agent, and an intermediate thereof: wherein R1represents a hydrogen atom or a carboxyl-protecting group; R2represents a substituted or unsubstituted alkyl, alkenyl, cycloalkyl, aryl or heterocyclic group; R3represents at least one group selected from hydrogen atom, halogen atoms, substituted or unsubstituted alkyl, alkenyl, cycloalkyl, aryl, alkoxy or alkylthio groups, nitro group, cyano group, acyl groups, protected or unprotected hydroxyl groups and protected or unprotected or substituted or unsubstituted amino groups; R4represents at least one group selected from hydrogen atom, halogen atoms, substituted or unsubstituted alkyl, alkenyl, cycloalkyl, aralkyl, aryl, alkoxy or alkylthio groups, protected or unprotected hydroxyl or imino groups, protected or unprotected or substituted or unsubstituted amino groups, alkylidene groups, oxo group and groups each forming a cycloalkane group together with the carbon atom to which R4bonds; R5represents a hydrogen atom, an amino-protecting group, a substituted or unsubstituted alkyl, cycloalkyl, alkylsulfonyl, arylsulfonyl, acyl or aryl group; R6represents a hydrogen atom, a halogen atom, a substituted or unsubstituted alkyl, alkoxy or alkylthio group, a protected or unprotected hydroxyl or amino group or a nitro group; and A represents CH or C—R7in which R7represents a halogen atom, a substituted or unsubstituted alkyl, alkoxy or alkylthio group or a protected or unprotected hydroxyl group, and to a salt of a 7-isoindoline-quinolonecarboxylic acid represented by the general formula [1], a hydrate thereof and a composition comprising them as an active ingredient.