CAS: 74163-81-8; (S)-1,2,3,4-Tetrahydroisoquinoline-3-Carboxylic Acid

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S-1,2,3,4-四氢异喹啉-3-羧酸苄酯盐酸盐置于sodium Hydroxide体系中,用 水 作为反应溶剂,化学反应 15.0H,以81%的收率获得产物(S)-(-)-1,2,3,4-四氢异喹啉-3-羧酸
参考文献:Efficient Synthesis Of Racemic And Enantiomerically Pure 1,2,3,4-Tetrahydroisoquinoline-3-Carboxylic Acid And Esters
标题:Efficient Synthesis Of Racemic And Enantiomerically Pure 1,2,3,4-Tetrahydroisoquinoline-3-Carboxylic Acid And Esters
摘要:在碱催化下,1,2-双(卤甲基)苯 1 A 或 B 与 2-(乙酰氨基)丙二酸二乙酯(2)发生环化反应,随后发生脱羧反应和酰胺裂解反应,制备出了外消旋和光学纯的 1,2,3,4-四氢异喹啉-3-羧酸及酯.对映体的分解是通过与(-)-薄荷醇酯化,然后柱层析分离非对映异构体混合物,或通过与扁桃酸分离苄酯的双酯盐,以及碱催化两种酯的皂化反应来实现的.
DOI:10.1055/s-1992-26325

专利信息

专利号:US-9233943-B2
优先权日:2012-01-10
标题:Process for synthesis of syn azido epdxide and its use as intermediate for the synthesis of amprenavir and saquinavir
发明人：GADAKH SUNITA KHANDERAO; REKULA REDDY SANTHOSH; SUDALAI ARUMUGAM
权利人:COUNCIL SCIENT IND RES
摘要:A novel synthetic route to the syn-azido epoxide of formula 5 includes cobalt-catalyzed hydrolytic kinetic resolution of a racemic mixture of the azido-epoxide. Reaction steps include subjecting an allylic alcohol to epoxidation with mCPBA to obtain a racemic epoxy alcohol; ring opening the epoxy alcohol with azide anion to obtain an anti-azido alcohol, which can then be selectively tosylated at the primary alcohol; treating the tosylate with base to obtain the racemic azido-epoxide; and subjecting the racemic azido-epoxide to cobalt-catalyzed hydrolytic kinetic resolution to obtain the syn-azido epoxide of formula 5. The compound of formula 5 may be used as a common intermediate for the asymmetric synthesis of HIV protease inhibitors, such as Amprenavir, Fosamprenavir, Saquinavir, and formal synthesis of Darunavir and Palinavir.

专利号:US-2024218014-A1
优先权日:2022-11-21
标 题:Synthesis of a cyclic peptide
发明人：BAUR PIUS BRUNO; CLEATOR EDWARD; DENIAU GILDAS; EISELE FRANK; FLÖGEL OLIVER; HUSTE ANJA; KEHL MARCEL ROMAN; LÖWENECK MARKUS; SILVA ROLANDO RAVELO; VORBERG RAFFAEL
权利人:JANSSEN PHARMACEUTICA NV
摘要:Processes for performing peptide synthesis, particularly for cyclic peptide synthesis are generally described. Reaction intermediates of the peptide synthesis are also described.

专利号:US-2023212788-A1
优先权日:2020-03-26
标 题:New method for automated on-demand biomolecular array synthesis
发明人：ZHANG YIXIN; LIN WEILIN
权利人:UNIV DRESDEN TECH
摘要:The invention provides an amphiphilic coating for the direct and rapid synthesis of an array of peptides and small molecular compounds on a planar surface of a solid support, comprising a hydrophilic chemical structure and a lipophilic group, wherein said peptides and small molecular compounds differ from spot to spot from each other in the chemical structure, characterized in that said amphiphilic coating possesses low wettability to polar aprotic solvents used in the array synthesis; said amphiphilic coating possessing low wettability is designed that it can be converted to a coating possessing high wettability by hydrolysis of the lipophilic group; and said amphiphilic coating comprises an amino group for the reaction with an electrophilic reagent. The invention further provides a solid support comprising said amphiphilic coating and a method for method for the direct and rapid synthesis of an array of peptides and small molecular compounds on a planar surface of a solid support, wherein said planar surface of a solid support comprises said amphiphilic coating. Said method includes the enhancing of the wettability of a glass surface to organic solvents to realize automated on-demand biomolecular array synthesis comprising both, peptides and small molecular compounds. The amphiphilic surface can be switched to a hydrophilic surface, resulting in high density arrays suitable for protein- and cell-based screening.

专利号:US-2023272006-A1
优先权日:2021-08-31
标题:Peptidomimetics and method of synthesis thereof
发明人：NEFZI ADEL
权利人:NEFZI ADEL; THE FLORIDA INTERNATIONAL UNIV BOARD OF TRUSTEES
摘要:The subject invention provides compounds, peptidomimetics, and methods of synthesis thereof. The subject invention provides the synthesis and use of guanidino acids and/or poly guanidino acids not only as vehicles for drug delivery but as toolbox for drug discovery. The peptidomimetic of the subject invention comprises oligo(guanidino acid)s or poly(guanidino acid)s with guanidines as peptide bond surrogates. The incorporation of the guanidine as amide bond surrogates offers significant differences in polarity, hydrogen bonding capability, and acid-base character.

专利号:US-6340760-B1
优先权日:1998-06-26
标题:Process for the preparation of (S)-N-tert-butyl-1,2,3,4-tetrahydroisoquinoline-3-carboxyamide
发明人：BELLANI PIETRO; FRIGERIO MARCO
权利人:CLARIANT LSM ITALIA S P A
摘要:A description is given here of a novel process for the synthesis of N-carboxyanhydride of formula VIby reacting (3S)-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid with triphosgene in dioxane; a description is also given of a process for the synthesis of (S)-N-tert-butyl-1,2,3,4-tetrahydroisoquinoline-3-carboxyamide by treating the N-carboxyanhydride VI so obtained with tert-butylamine.

专利号:US-2023391818-A1
优先权日:2020-11-05
标 题:Peptide synthesis method for suppressing defect caused by diketopiperazine formation
发明人：NOMURA KENICHI; KAGE MIRAI; TAMIYA MINORU; KANAZAWA JUNICHIRO
权利人:CHUGAI PHARMACEUTICAL CO LTD
摘要:Solid-phase synthesis of a peptide has a problem that a desired elongation reaction is prevented from proceeding by diketopiperazine and a 6-membered diamine skeleton compound formed when a protective group at the N-terminal is removed. The present inventors have found that when in production of a peptide by a solid-phase method, a peptide in which an amino group at the N-terminal is protected with a protective group having an Fmoc skeleton is treated in a specific solvent with a base having a pKa of 23 or more in acetonitrile as a conjugate acid, and a peptide chain is then elongated, it is possible to solve the problem described above.