Dissertation > Excellent graduate degree dissertation topics show

Synthesis of Antibiotics Drug-Pirlimycin

Author: TaoGuoJian
Tutor: YangYiWen
School: Zhejiang University
Course: Pharmaceutical Engineering
Keywords: Lincosamide antibiotics Pirlimycin 7-C1-MTL Hydrazinolysis Hydrogenation Chlorination
CLC: TQ465
Type: Master's thesis
Year: 2010
Downloads: 55
Quote: 0
Read: Download Dissertation

Abstract


Pirlimycin (CAS No.:78822-40-9) is a lincosamide antibiotic developed by Pharmacia & Upjohn Company (now Pfizer) for the treatment of Gram-positive bacteria-induced bovine mastitis.In this thesis, a novel efficient synthetic method was reported for the preparation of pirlimycin with high purity. The synthetic procedure included the following steps:(a) the preparation of 4-ethyl-2-cyanopyridine from 4-ethyl pyridine via oxidation and cyanation; (b) the synthesis of 4-ethylpiperidine-2-carboxylic acid from 4-ethyl-2-cyanopyridine through esterification, hydrogenation, and hydrolysis reactions; (c) the protection of 4-ethylpiperidine-2-carboxylic acid with chloroformate to produce the N-substituted piperidine-2-carboxylic acid derivative; (d) the formation of 7-chloro-l-methylthio-lincosamine (7-C1-MTL) via the hydrazinolysis of lincomycin and subsequent chlorination; (e) the condensation of N-substituted piperidine-2-carboxylic acid derivatives with 7-Cl-MTL to furnish the pirlimycin intermediate; (f) the Pd/C-catalyzed hydrogenation of the pirlimycin intermediate to obtain the target product---pirlimycin.Based on cis-4-ethyl-piperidine-2-formic acid as starting material, a total yield of 37.3% was obtained with about 98% purity pirlimycin. The total yield was 26.1% when the product purity was 99%. The process has a lower cost of raw materials, more suitable for commercial production.

Related Dissertations

  1. Degradation of microcystin and Elimination Methods,X173
  2. High hydrothermal stability of nickel-based catalyst and hydrogenation of butyne diol,TQ223.162
  3. Synthesis of 2-methyl-4-methoxylaniline by Pt/C Catalytic Hydrogenation,TQ246.31
  4. Continuous Synthesis of 2,3-Dichloropyridine in a Microreaction System,TQ253.2
  5. Study on the Kinetics of Acetic Acid Hydrogenation to Ethanol,TQ223.122
  6. Study on Purification Process of Caprolactam Produced with Toluene,TQ225.261
  7. Study on Nickel-based Catalysts for Selective Hydrogenation,TQ203.2
  8. Synthesis of 5,6-diaminobenzimidazolone,TQ25
  9. Research of Removal Groups of Lignin Model Compounds,TQ203.2
  10. Study on Preparation and Performance of Ni-based Structured Catalyst for Synthesis of m-Phenylenediamine by Catalytic Hydrogenation,TQ426.65
  11. Study on Preperation, Characterization and Application of Pd/γ-Al2O3/Cordierite Monolith Catalyst,TQ426
  12. Preparation and Biocompatibility of Tantalum Oxide Films,R318.08
  13. The Preparation of Chitosan-palladium Complex & the Kinetic Study on Catalytic Hydrogenation of Ketones,O643.3
  14. Catalytic asymmetric hydrogen transfer synthesis of chiral and asthma drug salmeterol,TQ463.2
  15. Ring-Chlorination of Toluene and Isomerization Reaction of O-Chlorotoluene over ZSM-5 Zeolite,TQ242
  16. Study on Immobilized of Photosynthetic Bacteria and Asymmetric Hydrogenation of Acetophenone,Q814.2
  17. Study on Stepwise Method of Disinfection for Raw Water Polluted by Micro-Organism in Period of Post-Earthquake Reconstruction,TU991.25
  18. Synthesis of novel chiral catalysts for asymmetric hydrogenation and catalytic properties,O643.32
  19. Study on Ru Catalytic Hydrogenation of Carbon Dioxide for Direct Synthesis of Formic Acid in Consecutive Reaction,TQ225.121
  20. The Optimization of the Coking Crude Benzol Hydro-refining Extractive Distillation Process,TQ522.62

CLC: > Industrial Technology > Chemical Industry > Pharmaceutical chemical industry > Antibiotics manufacture
© 2012 www.DissertationTopic.Net  Mobile