55747-45-0

Usage

Uses

Used in Pharmaceutical Industry:
ETHYL 2-(3-N-PHTHALIMIDOPROPYL)ACETOACETATE is used as a key intermediate in the synthesis of Zolmitriptan and its related compounds. Zolmitriptan is a selective agonist of the 5-HT1B and 5-HT1D receptors, which are involved in the treatment of migraine and cluster headaches. ETHYL 2-(3-N-PHTHALIMIDOPROPYL)ACETOACETATE plays a crucial role in the production of these medications, enabling the development of effective treatments for these debilitating conditions.

InChI:InChI=1/C17H19NO5/c1-3-23-17(22)12(11(2)19)9-6-10-18-15(20)13-7-4-5-8-14(13)16(18)21/h4-5,7-8,12H,3,6,9-10H2,1-2H3

Upstream product

• 5460-29-7 2-(3-bromopropyl)isoindole-1,3-dione 
• 1007476-32-5 sodium ethyl acetylacetate enolate 
• 141-97-9 ethyl acetoacetate 
• 42251-84-3 N-(3-chloropropyl)phthalimide 
• 5457-29-4 N-(3-iodopropyl)phthalimide 
• 88-00-6 ethyl 2,4-dichloro-3-oxobutanoate 
• 136918-14-4 phthalimide 
• 142-28-9 1,3-Dichloropropane 

Downstream Products

• 55747-53-0 2-ethoxycarbonyl-3-(2-phthalimidoethyl)-5-methoxyindole 
• 96277-44-0 6-benzyloxy-3-(2-phthalimido-ethyl)-indole-2-carboxylic acid ethyl ester 
• 96277-43-9 5-benzyloxy-3-(2-phthalimido-ethyl)-indole-2-carboxylic acid ethyl ester 
• 55747-48-3 2-phenylhydrazono-5-phthalimido-pentanoic acid ethyl ester 

Relevant academic research and scientific papers

A Radical Bidirectional Fragment Coupling Route to Unsymmetrical Ketones

A powerful strategy for the regioselective bidirectional synthesis of unsymmetrically substituted ketones is described, relying on the fact that the exchange of a xanthate is much faster than the radical addition to an unactivated alkene. The use of an alkene as the formal "alkylating" agent associated with the tolerance for numerous functional groups and the mildness of the experimental conditions removes many of the problems associated with the classical ionic and transition-metal-based approaches.

Preparation method of melatonin

The invention relates to the technical field of chemical synthesis of medicines, in particular to a preparation method of melatonin. The preparation method of the melatonin comprises the following steps: (a) subjecting phthalimide, 1,3-dichloropropane, sodium iodide and ethyl acetoacetate to a reaction in a solvent under the action of alkali to obtain a compound I; (b) performing a ring closing reaction on the compound I and p-methoxyphenyl diazonium salt in the presence of alkali and a solvent to obtain a compound II; (c) hydrolyzing the compound II under an alkaline condition, and carrying out decarboxylating under an acidic condition to obtain a compound III; and (d) carrying out an acetylation reaction on the compound III to obtain melatonin. According to the preparation method, phthalimide, 1,3-dichloropropane, ethyl acetoacetate and the like are used as raw materials, and the price of the raw materials is low; the intermediate compound I can be obtained through a one-step method,so reaction steps and time are shortened; moreover, the conditions of each reaction step are relatively mild, the raw materials are easy to obtain, and high yield can be obtained.

Novel Electrophilic and Photoaffinity Covalent Probes for Mapping the Cannabinoid 1 Receptor Allosteric Site(s)

Undesirable side effects associated with orthosteric agonists/antagonists of cannabinoid 1 receptor (CB1R), a tractable target for treating several pathologies affecting humans, have greatly limited their translational potential. Recent discovery of CB1R negative allosteric modulators (NAMs) has renewed interest in CB1R by offering a potentially safer therapeutic avenue. To elucidate the CB1R allosteric binding motif and thereby facilitate rational drug discovery, we report the synthesis and biochemical characterization of first covalent ligands designed to bind irreversibly to the CB1R allosteric site. Either an electrophilic or a photoactivatable group was introduced at key positions of two classical CB1R NAMs: Org27569 (1) and PSNCBAM-1 (2). Among these, 20 (GAT100) emerged as the most potent NAM in functional assays, did not exhibit inverse agonism, and behaved as a robust positive allosteric modulator of binding of orthosteric agonist CP55,940. This novel covalent probe can serve as a useful tool for characterizing CB1R allosteric ligand-binding motifs.

Practical and phase transfer-catalyzed synthesis of 6-methoxytryptamine

A convenient and cost-effective synthesis of 6-methoxytryptamine (1), starting from commercially available phthalimide and 1-bromo-3-chloropropane via PTC N-alkylation, PTC C-alkylation, Japp-Klingemann reaction, hydrolysis, and decarboxylation, has been accomplished with a 44% overall yield. Copyright Taylor & Francis Group, LLC.

Microwave assisted synthesis of melatonin

Melatonin was prepared from phthalimide by N- and C-alkylation, cyclization, hydrolytic, decarboxylation, and acetylation. The four-pot reactions were carried out on microwave irradiation in good yield with short time.

Process research and development of melatonin

A short, simple, and industrially feasible process for the preparation of melatonin (N-acetyl-5-methoxy tryptamine), starting from phthalimide and 1-bromo-3-chloropropane, in essentially four steps is discussed. The present article elucidates the preparative process along with the impurity profile of each intermediate.