experiment 57

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Feb 20, 2024

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CHEM 324 Organic Reactions Experiment 57 Using the Chemical Literature in an Organic Synthesis Jiani He 26380107 Performed Thursday 09/21/2023 Submitted on Thursday 09/28/2023

1. What is the CAS Registry Number of your target compound? It is 62571-86-2. 2. Draw its structure. 3. Give at least one synonym for your compound. (S)-1-((S)-3-mercapto-2-methylpropanoyl)pyrrolidine-2-carboxylic acid L-Proline, 1-[(2S)-3-mercapto-2-methyl-1-oxopropyl]- 4. Use SciFinder to locate an article that outlines a multi-step synthetic pathway for making your compound. Provide a printout or photocopy of the first page of the article. a. Write out two steps of the reaction giving compound names and their structures. 1 1 : (S)-proline 2 : N-acryloyl-(S)-proline 3 : β-Hydroxy-α-methylene-N-acryloyl-(S)-proline b. Provide the reaction conditions. 1 In the first step, an ice-bath was used to cool a stirred solution of 1 (43 mmol, 5 g) in 2 M aqueous potassium hydroxide (52 mmol, 26 mL). Acetone (26 mL) was used to dilute the solution. Over the course of 40 minutes, 2 M aqueous potassium hydroxide (61 mmol, 30 mL) and an acetone solution (26 mL) of acryloyl chloride (48 mmol, 4.34 g) were added simultaneously to the stirred mixture. The reaction was allowed to reach room temperature and react for 3 h, after which the product, 2 , was isolated, purified and characterized. In the second step, 2 (1.89 mmol, 0.472 g) was dissolved in tetrahydrofuran (10 mL), followed by the addition of 5 mL of 40% aqueous formaldehyde (54.28 mmol, 1.63 g). The mixture was sonicated for 48 h before isolation, purification and characterization were performed. c. Include amounts of reactants and product yield. In the first step, the reactants are 5 g of (S)-proline (1.00 eqv) and 4.34 g of acryloyl chloride (1.12 eqv); the percent yield of this step is 70%. 1 In the second step, the reactants are 0.472 g of (S)-1- acryloylpyrrolidine-2-carboxylic acid (1.00 eqv) and 1.63 g of formaldehyde (28.72 eqv); the percent yield of this step is 93%. 1

D 5. What is your compound used for? Is it produced naturally? If so, indicate its source. The compound is used in the treatment of hypertension as it is an angiotensin-converting enzyme inhibitor. 2 Patented in 1977, the compound is developed and synthesized in the laboratory and not found in nature. 2 6. In a laboratory setting, you would want to confirm the identity of your compound by measuring its physical properties. Provide the melting point and/or boiling point of your compound, and a printout or reference to one type of spectral parameter (if available, e.g. IR, UV, MS). If a melting point or boiling point is not available, provide an additional physical property (e.g. TLC, [α] D ). Melting point: 103 − 105 ℃ . 3 [α]22: −131.0 (c = 1.7, s = EtOH). 4 The infrared spectrum is shown below. 5

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Reference 1. Feltrin, M. P.; Almeida, W. P. A Synthesis of Captopril Through a Baylis-Hillman Reaction. Synth. Commun. 2003 , 33(7), 1141-1146. 2. The Merck Index: An Encyclopedia of Chemicals, Drugs, and Biologicals , 15th ed.; Budavari, S.; O'Neal, M.J.; Smith, A.; Heckelman, P. E.; Kinneary, J. F., Eds.; Merck & Co.: Whitehouse Station, NJ, 2013; entry 1776. 3. SciFinder ; Chemical Abstracts Service: Columbus, OH; experimental melting point; RN 62571- 86-2; https://scifinder.cas.org (accessed September 24, 2023). 4. SciFinder ; Chemical Abstracts Service: Columbus, OH; experimental optical rotation; RN 62571- 86-2; https://scifinder.cas.org (accessed September 24, 2023). 5. Spectral Database for Organic Compounds (SDBS) ; infrared spectrum; SDBS No.: 16831; RN 62571-86-2; https://sdbs.db.aist.go.jp/sdbs/cgi-bin/cre_index.cgi/ (accessed September 24, 2023).