{"product_id":"synthesis-of-chemical-compounds-results-discussion-and-experimental-section-von-sadik-mejid","title":"Synthesis of Chemical Compounds. Results, Discussion and Experimental Section","description":"\u003cp\u003eInternship Report from the year 2015 in the subject Chemistry - Organic Chemistry, grade: 1,3, University of Cologne (Institut für Organische Chemie), language: English, abstract: A literature survey via Reaxys revealed 2 references in which this compound was described as the product. The first synthesis has been published by Corey in the  Journal of Organic Chemistry in 1988: N-(benzyloxycarbonyl)-(S)-proline (3) was synthesized in 75.2% yield from proline by reaction with benzyl chloroformate in an aqueous solution at 0¿5°C. E. J. Corey, J. Org. Chem., Vol. 53, No. 12, 1988, 2861-2863 seemed to be the best choice for its high yield.\u003c\/p\u003e\u003cp\u003e\u003c\/p\u003e\u003cp\u003eThe protection of proline with benzylchloroformate gave a colourless solid, which recrystallized from petrolium ether. The yield of 75.2% is below that reportedin the literature (96%). The purity of the product could not be proofed, since no enough analytic data are available. For the product (3) no GC-MS was recorded, because of its carbon acid group that might damage the mass spectrometry system.\u003c\/p\u003e\u003cp\u003e\u003c\/p\u003e\u003cp\u003eThe hydroxide ion of NaOH deprotonates the NH-group of proline to form water and the electron pair of the nitrogen anion undergo a nucleophilic attack to the carbon atom of the carbonyl-group to give (3). The sodium cation forms with chloride anion sodiumchloride that prcipitates. An example for the application of the cyclic amino acid is its use as a pharmaceutical intermidiate, which is used for the synthesis of Eletriptan, a drug for the treatment of migriane.\u003c\/p\u003e\u003cdiv class=\"aw-variant-hidden-subtitle-div\" id=\"aw-variant-subtitle-9783668965195\"\u003e\u003ch3\u003e\u003c\/h3\u003e\u003c\/div\u003e","brand":"Libri","offers":[{"title":"Softcover - 9783668965195","offer_id":39437587087453,"sku":"9783668965195","price":12.99,"currency_code":"EUR","in_stock":true}],"thumbnail_url":"\/\/cdn.shopify.com\/s\/files\/1\/0940\/0622\/files\/2f56a3d1-e92c-454c-8b46-670e9ad87882.jpg?v=1773899440","url":"https:\/\/shop.autorenwelt.de\/en\/products\/synthesis-of-chemical-compounds-results-discussion-and-experimental-section-von-sadik-mejid","provider":"Autorenwelt Shop","version":"1.0","type":"link"}