New Methodology for the synthesis of chloramphenicol

Material Information

Title:
New Methodology for the synthesis of chloramphenicol
Series Title:
Student Symposium 2016
Creator:
Elhalaby, Nancy ( Author, Primary )
Ghosh, Phalguni ( Advisor )
Lavey, Brian ( Advisor )
Middlesex College, Department of Natural Sciences ( Sponsor )
Place of Publication:
Edison, NJ
Publisher:
Middlesex College
Publication Date:

Subjects

Subjects / Keywords:
College students -- poster presentations ( lcsh )
Student Works -- Natural Sciences -- poster presentations ( lcsh )
Chemistry ( lcsh )
Biochemistry ( lcsh )
Middlesex College (Edison, NJ) -- Student works
Middlesex County College (Edison, NJ) ( lcsh )
Student Works -- Natural Sciences -- academic theses
Temporal Coverage:
Academic Year 2016-2017 ( 2016 - 2017 )
Spatial Coverage:
New Jersey -- Edison

Notes

Abstract:
For this project, we attempted a new synthesis of Chloramphenicol, An antibiotic used that inhibits the protein synthesis in bacteria. This involves a series of reactions, some of which were to create materials which were unavailable to us, and some of which were essential to the production of the compound. First, we carried out an acylation reaction between Dichloroacetyl Chloride and Aminoacetaldehyde dimethyl acetal with triethylamine to act as a base and ethyl acetate as a solvent. Then, that product underwent a hydrolysis using THF and 2M HCl to convert the acetal to an aldehyde which went in about 75% yield. L-proline was then used to catalyze a reaction in conjunction with DMSO to add 1 equivalent of P-nitrobenzaldehyde to the aldehyde product, which should result in one hydroxyl group facing forward and another one facing backward. L-proline acts to add the hydroxyl groups in a stereochemically-specific way, which should be the D-threo conformation. That reaction was based on a publishing in the Journal of the American Chemical Society by Carlos F. Barbas III, et al. The next reaction involved reduction by Sodium Borohydride to reduce the aldehyde to the corresponding alcohol.

Record Information

Source Institution:
Middlesex County College Institution
Holding Location:
Middlesex County College Institution
Rights Management:
All applicable rights reserved by the source institution and holding location.

MCC Membership

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