Synthetic Route of C10H13ClO3《Design, synthesis and biological evaluation of novel azaspiro analogs of linezolid as antibacterial and antitubercular agents》 was published in 2016. The authors were Gadekar, Pradip K.;Roychowdhury, Abhijit;Kharkar, Prashant S.;Khedkar, Vijay M.;Arkile, Manisha;Manek, Hardik;Sarkar, Dhiman;Sharma, Rajiv;Vijayakumar, V.;Sarveswari, S., and the article was included in《European Journal of Medicinal Chemistry》. The author mentioned the following in the article:
The design, synthesis and antimicrobial evaluation of a novel series of azaspiro analogs I [R = acetyl, 4-(trifluoromethyl)benzoyl, nicotinoyl, etc.] of linezolid were described. Linezolid comprises of a morpholine ring which was known for its metabolism-related liabilities. Therefore, the key modification made in the linezolid structure was the replacement of morpholine moiety with its bioisostere, 2-oxa-6-azaspiro[3.3]heptane. Furthermore, the replacement of N-acetyl terminal of linezolid with various aromatic or aliphatic functionalities was carried out. The title compounds were evaluated against a panel of Gram-pos. and Gram-neg. bacteria and Mycobacterium tuberculosis. Subsequent structure-activity relationship (SAR) studies identified several compounds with mixed antibacterial and antitubercular profiles. Compound I [R = isoxazole-5-carbonyl] (IC50 0.72, 0.51, 0.88, 0.49 μg/mL for Escherichia coli, Pseudomonas aeruginosa, Staphylococcus aureus, Bacillussubtilis, resp.) exhibited similar antibacterial profile as linezolid. The N-acetyl derivative I [R = acetyl] was similar to linezolid in antitubercular profile. The use of azaspiro substructure in the medicinal chem. of antibacterial and antitubercular agents was demonstrated.(1S)-4,7,7-Trimethyl-3-oxo-2-oxabicyclo[2.2.1]heptane-1-carbonyl chloride(Chunks or pellets) (cas: 39637-74-6) were involved in the experimental procedure.
(1S)-4,7,7-Trimethyl-3-oxo-2-oxabicyclo[2.2.1]heptane-1-carbonyl chloride(Chunks or pellets) (cas: 39637-74-6 Synthetic Route of C10H13ClO3) is used as a resolving agent for alcohols as the diastereomeric esters by crystallization or chromatography and as a chiral derivatization reagent for determination of enantiomeric excess of alcohols and amines.
Reference:
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics