This report is a laboratory experiment, please explain it in detail, knowing that this topic is for medicinal chemistry
Posted: Wed May 18, 2022 9:45 am
This report is a laboratory experiment, please explain it in detail, knowing that this topic is for medicinal chemistry and all the information is in the pictures
Please pay attention to the last three pictures because the experiment must be done according to the last three pictures Note: The English language is available, but some pages are written in Chinese and English
Note: Focus on the English language only and do not focus on the Chinese language because they have the same meaning, but only focus on the Chinese language
Experiment 2 Synthesis of Nifedipine
Purpose • Be familiar with the general process of pharmaceutical API preparatio n • Be familiar with intermediate control methods in drug preparation pr ocess • Understand the synthesis of dihydropyridine compounds and the appl ication of Hanstzch reaction in the production of dihydropyridine cardi ovascular drugs
Background • Nifedipine is first generation 1,4-dihydropyridine calcium antagonist. I t is widely used drug for the treatment of hypertension and stenocard ia. • Nifedipine is sparingly soluble in water solution Molecular Formula Molecular Weight Flash Point Exact Mass C,H,O, 346.335 241.2428.7 °C 346.116486 110.45000 2.97 PSA LogP
Experimental principles • Nifedipine was synthesized by condensation of ethyl acetoacetate, o-n itrobenzaldehyde and ammonia CH3COCH_COOCH3 + NH3 + CHO CH,00C HC- -NO -COOCH -CH3 NO2
Mechanism • Nifedipine is a dihydropyridine derivative in structure. It can be synthe sized from 2 Molecular ketoacids, 1 molecular aldehydes and 1 molec ular ammonia by hanstzch reaction. The mechanism is as follows: COCH.COM ROCCORD SCHOOR SH A 2010 ROCH.COM.CO CO ROC CH CR ROC CO ROOC ROOC ROOC
Reagents and specifications • O-nitrobenzaldehyde CP or AR 2 98% • molecular weight 151.12, light yellow acicular crystal, melting point 44 - 46 °C, boiling point 153 °C / 3.06 kPa, slightly soluble in water, soluble in alcoho 1, ether and benzene • methyl acetoacetate C.P. or AR 97% . molecular weight 116.11, colorless transparent liquid, boiling point 169 ~ 171 °C, n 1.418, D 1.0785, colorless transparent liquid, aromatic, slightly soluble i n water and easily soluble in organic solvents. • Ammonia C.P. or AR 25 ~ 28% • Methanol C.P. or AR
Experimental procedures • 100ml pear shaped bottle equipped with a reflux condenser and electromagnetic stir rer • 7.6g (0.05mol) of o-nitrobenzaldehyde, 13ml (0.12mol) of methyl acetoacetate, 15ml of methanol and 6ml (0.08mol) of ammonia (25 - 28%,D 0.91) successively added to the reaction bottle • Heat slowly under stirring, and then reflux after 0.5h • After 2h of reaction, take a little mixture reactant and check the reaction by TLC chro matography. Until the reactant reaction is complete, the whole reflux process takes a bout 3h. Cool to 5 °C, precipitate yellow crystals, keep heat for 1h, filter with funnel, wash wit h a small amount of ice methanol to obtain crude products, dry them as much as pos sible and weigh
Experimental procedures • The crude product is recrystallized by 7-8 times the volume (ml/g) of methanol • If necessary, it can be filtered while hot, standing, cooled (~ 5 °C), filte red, washed with a little ice methanol, and dried at 75 °C, to obtain 1 0 - 12g light yellow crystals • Measure the melting point (171 - 175 °C) and nuclear magnetic reson ance (solvent: CDC13). • Calculate the yield.
Final Report Template: 1. Abstract 2. Keywords 3. Introduction and Purpose 4. Experimental Procedures 5. Result and Discussion 6. Conclusion 7. Reference
dal 附录1 预习报告格式 to Appendix 1. Pre-lab Preparation A bound notebook should be used for the pre-lab preparation and recording experi- mental data. A spiral-bound notebook or sheet is not acceptable. The note book should have consecutively numbered paged; if it does not, you should number the pages previ- ously. 实验题目 * Experimental Title rimental Titletuumba 1. XHA9 Purpose 2. ** Experimental Principles 3. 所用试剂 Realents SUMATOS Names Characteristics b. p. or m. p. Solubility Toxicity Amounts Mol Equivalent Notes 4. IX Equipments Equipment diagrams are recommended. 5. 实验步骤流程 Experimental Steps A flow diagram is recommended. The notes and comments should be included. 6. ** Experimental Procedures sodel The procedures, phenomenon and data are recorded here. (北京大学药学院 李正香)
华中科技大学同济医学院 实很告 *. STRESS 事。 难小姐 FACETINIDE 2012_4_00_26_0 姓名 PRO To understasel the general Hyatial and chemical pmportues of Neuela musk and to be how to purify the product by using these properties 2. To master the principle and the operation of acetylatria. HALD (sco), HN -SN 21 --N-COCHE NA ON 18 NAOH HON SOUNHCOCH, 50N-COCHE som Na Mol Mol nabib 1 EXPERIMENTATION Materials Materials ufanilande cht wydride zdium hydroxide odium hydrovide Specification CP CP 22.5% 7720 Aucunct 17.2g 13.6ml 1.4 0.14 22.nl 0.11 0.17 12.sal 1.9 PERATIONS a aflesing ordense and a auly donde 3.bul is To a 3 mock et flost, quipped with a china add Hermometer, add sulfum tenete 193.77 and 22.5% sedium boy cer xidle aquesta olution and are placed. The reaction muxture io strued and heated to about soe ya water south at the me time After the sound in the mixture is desolved, acceture added in dop wire. After s mindes, 9.7% soeterm hyclooride any new collection are added in ар Eropwx way o munales alternately, a ml each time kept between a and B and the temperature should be munnused between So'? and so alwaing soldation of acetic and drdo anel scelei hyderside solution The pH of the solution should we
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Note: Focus on the English language only and do not focus on the Chinese language because they have the same meaning, but only focus on the Chinese language
Experiment 2 Synthesis of Nifedipine
Purpose • Be familiar with the general process of pharmaceutical API preparatio n • Be familiar with intermediate control methods in drug preparation pr ocess • Understand the synthesis of dihydropyridine compounds and the appl ication of Hanstzch reaction in the production of dihydropyridine cardi ovascular drugs
Background • Nifedipine is first generation 1,4-dihydropyridine calcium antagonist. I t is widely used drug for the treatment of hypertension and stenocard ia. • Nifedipine is sparingly soluble in water solution Molecular Formula Molecular Weight Flash Point Exact Mass C,H,O, 346.335 241.2428.7 °C 346.116486 110.45000 2.97 PSA LogP
Experimental principles • Nifedipine was synthesized by condensation of ethyl acetoacetate, o-n itrobenzaldehyde and ammonia CH3COCH_COOCH3 + NH3 + CHO CH,00C HC- -NO -COOCH -CH3 NO2
Mechanism • Nifedipine is a dihydropyridine derivative in structure. It can be synthe sized from 2 Molecular ketoacids, 1 molecular aldehydes and 1 molec ular ammonia by hanstzch reaction. The mechanism is as follows: COCH.COM ROCCORD SCHOOR SH A 2010 ROCH.COM.CO CO ROC CH CR ROC CO ROOC ROOC ROOC
Reagents and specifications • O-nitrobenzaldehyde CP or AR 2 98% • molecular weight 151.12, light yellow acicular crystal, melting point 44 - 46 °C, boiling point 153 °C / 3.06 kPa, slightly soluble in water, soluble in alcoho 1, ether and benzene • methyl acetoacetate C.P. or AR 97% . molecular weight 116.11, colorless transparent liquid, boiling point 169 ~ 171 °C, n 1.418, D 1.0785, colorless transparent liquid, aromatic, slightly soluble i n water and easily soluble in organic solvents. • Ammonia C.P. or AR 25 ~ 28% • Methanol C.P. or AR
Experimental procedures • 100ml pear shaped bottle equipped with a reflux condenser and electromagnetic stir rer • 7.6g (0.05mol) of o-nitrobenzaldehyde, 13ml (0.12mol) of methyl acetoacetate, 15ml of methanol and 6ml (0.08mol) of ammonia (25 - 28%,D 0.91) successively added to the reaction bottle • Heat slowly under stirring, and then reflux after 0.5h • After 2h of reaction, take a little mixture reactant and check the reaction by TLC chro matography. Until the reactant reaction is complete, the whole reflux process takes a bout 3h. Cool to 5 °C, precipitate yellow crystals, keep heat for 1h, filter with funnel, wash wit h a small amount of ice methanol to obtain crude products, dry them as much as pos sible and weigh
Experimental procedures • The crude product is recrystallized by 7-8 times the volume (ml/g) of methanol • If necessary, it can be filtered while hot, standing, cooled (~ 5 °C), filte red, washed with a little ice methanol, and dried at 75 °C, to obtain 1 0 - 12g light yellow crystals • Measure the melting point (171 - 175 °C) and nuclear magnetic reson ance (solvent: CDC13). • Calculate the yield.
Final Report Template: 1. Abstract 2. Keywords 3. Introduction and Purpose 4. Experimental Procedures 5. Result and Discussion 6. Conclusion 7. Reference
dal 附录1 预习报告格式 to Appendix 1. Pre-lab Preparation A bound notebook should be used for the pre-lab preparation and recording experi- mental data. A spiral-bound notebook or sheet is not acceptable. The note book should have consecutively numbered paged; if it does not, you should number the pages previ- ously. 实验题目 * Experimental Title rimental Titletuumba 1. XHA9 Purpose 2. ** Experimental Principles 3. 所用试剂 Realents SUMATOS Names Characteristics b. p. or m. p. Solubility Toxicity Amounts Mol Equivalent Notes 4. IX Equipments Equipment diagrams are recommended. 5. 实验步骤流程 Experimental Steps A flow diagram is recommended. The notes and comments should be included. 6. ** Experimental Procedures sodel The procedures, phenomenon and data are recorded here. (北京大学药学院 李正香)
华中科技大学同济医学院 实很告 *. STRESS 事。 难小姐 FACETINIDE 2012_4_00_26_0 姓名 PRO To understasel the general Hyatial and chemical pmportues of Neuela musk and to be how to purify the product by using these properties 2. To master the principle and the operation of acetylatria. HALD (sco), HN -SN 21 --N-COCHE NA ON 18 NAOH HON SOUNHCOCH, 50N-COCHE som Na Mol Mol nabib 1 EXPERIMENTATION Materials Materials ufanilande cht wydride zdium hydroxide odium hydrovide Specification CP CP 22.5% 7720 Aucunct 17.2g 13.6ml 1.4 0.14 22.nl 0.11 0.17 12.sal 1.9 PERATIONS a aflesing ordense and a auly donde 3.bul is To a 3 mock et flost, quipped with a china add Hermometer, add sulfum tenete 193.77 and 22.5% sedium boy cer xidle aquesta olution and are placed. The reaction muxture io strued and heated to about soe ya water south at the me time After the sound in the mixture is desolved, acceture added in dop wire. After s mindes, 9.7% soeterm hyclooride any new collection are added in ар Eropwx way o munales alternately, a ml each time kept between a and B and the temperature should be munnused between So'? and so alwaing soldation of acetic and drdo anel scelei hyderside solution The pH of the solution should we