2-(Tert-butoxycarbonyl)-1,2,3,4-tetrahydroisoquinoline-6-carboxylic acid

Base Information

• Chemical Name: 2-(Tert-butoxycarbonyl)-1,2,3,4-tetrahydroisoquinoline-6-carboxylic acid
• CAS No.: 170097-67-3
• Molecular Formula: C15H19NO4
• Molecular Weight: 277.32
• Hs Code.: 2933499090
• European Community (EC) Number: 676-412-5
• DSSTox Substance ID: DTXSID20463496
• Wikidata: Q72450804
• Mol file: 170097-67-3.mol

Synonyms:170097-67-3;2-(tert-butoxycarbonyl)-1,2,3,4-tetrahydroisoquinoline-6-carboxylic acid;N-Boc-1,2,3,4-tetrahydroisoquinoline-6-carboxylic acid;3,4-Dihydro-1H-isoquinoline-2,6-dicarboxylic acid 2-tert-butyl ester;2-[(2-methylpropan-2-yl)oxycarbonyl]-3,4-dihydro-1H-isoquinoline-6-carboxylic Acid;2-Boc-1,2,3,4-Tetrahydroisoquinoline-6-Carboxylic Acid;2-BOC-1,2,3,4-TETRAHYDRO-ISOQUINOLINE-6-CARBOXYLIC ACID;MFCD05861548;UHOIFEOHBGCPHE-UHFFFAOYSA-N;SCHEMBL306991;DTXSID20463496;2-tert-butoxycarbonyl-3,4-dihydro-1H-isoquinoline-6-carboxylic acid;AKOS015909489;CS-W005911;PB20129;AM803316;DS-12491;SY036194;A3755;FT-0650113;A20056;EN300-268882;J-010596;n-boc-6-hydroxycarbonyl-1,2,3,4-tetrahydroisoquinoline;4-((3-fluorophenyl)amino)-2-methylpiperidine-4-carbonitrile;2-(tert-butoxycarbonyl)-1,2,3,4-tetrahydroisoquinoline-6-carbonic acid;2-(tert-butoxycarbonyl)-1,2,3,4-tetrahydroisoquinoline-6-carboxylicacid;2-[(tert-butoxy)carbonyl]-1,2,3,4-tetrahydroisoquinoline-6-carboxylic acid;2-{[(1,1-dimethylethyl)oxy]carbonyl}-1,2,3,4-tetrahydro-6-isoquinoline carboxylic acid;2-{[(1,1-dimethylethyl)oxy]carbonyl}-1,2,3,4-tetrahydro-6-isoquinolinecarboxylic acid;2-{[(2-Methyl-2-propanyl)oxy]carbonyl}-1,2,3,4-tetrahydro-6-isoquinolinecarboxylic acid;462070-49-1

Chemical Property of 2-(Tert-butoxycarbonyl)-1,2,3,4-tetrahydroisoquinoline-6-carboxylic acid

Chemical Property:

• Vapor Pressure: 3.93E-08mmHg at 25°C
• Refractive Index: 1.563
• Boiling Point: 429.3 °C at 760 mmHg
• PKA: 4.33±0.20(Predicted)
• Flash Point: 213.4 °C
• PSA: 66.84000
• Density: 1.221 g/cm³
• LogP: 2.61590
• Storage Temp.: 2-8°C
• XLogP3: 2.2
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 3
• Exact Mass: 277.13140809
• Heavy Atom Count: 20
• Complexity: 388

Purity/Quality:

99% ^*data from raw suppliers

N-Boc-1,2,3,4-Tetrahydroisoquinoline-6-carboxylicAcid ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)(C)OC(=O)N1CCC2=C(C1)C=CC(=C2)C(=O)O
• Uses: N-Boc-1,2,3,4-Tetrahydroisoquinoline-6-carboxylic Acid is the starting material used to prepare benzazole derivatives as β-secretase inhibitors useful in treatment and prevention of diseases.

Technology Process of 2-(Tert-butoxycarbonyl)-1,2,3,4-tetrahydroisoquinoline-6-carboxylic acid

There total 17 articles about 2-(Tert-butoxycarbonyl)-1,2,3,4-tetrahydroisoquinoline-6-carboxylic acid which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 99.0%

3,4-Dihydro-1H-isoquinoline-2.6-dicarboxylic acid 2-tert-butyl ester-6-methyl ester (170097-66-2) → 2-(tert-butoxycarbonyl)-1,2,3,4-tetrahydroisoquinoline-6-carboxylic acid (170097-67-3)

Guidance literature:

With sodium hydroxide; In tetrahydrofuran; methanol; for 3h; Heating;

DOI:10.1021/jm049884d

Reference yield: 80.0%

di-tert-butyl dicarbonate (24424-99-5) + tetrahydroisoquinoline-6-carboxylic acid → 2-(tert-butoxycarbonyl)-1,2,3,4-tetrahydroisoquinoline-6-carboxylic acid (170097-67-3)

Guidance literature:

With sodium carbonate; In 1,4-dioxane; water; at 25 ℃; for 24h; Solvent;

Reference yield: 49.0%

6-bromo-2-(tert-butoxycarbonyl)-1,2,3,4-tetrahydroisoquinoline (893566-74-0) + carbon dioxide (124-38-9,18923-20-1) → 2-(tert-butoxycarbonyl)-1,2,3,4-tetrahydroisoquinoline-6-carboxylic acid (170097-67-3)

Guidance literature:

6-bromo-2-(tert-butoxycarbonyl)-1,2,3,4-tetrahydroisoquinoline; With n-butyllithium; In tetrahydrofuran; hexane; at -78 ℃; Inert atmosphere;

carbon dioxide; In tetrahydrofuran; hexane; at 20 ℃; for 18h;

DOI:10.1021/acs.jmedchem.1c01585

upstream raw materials:

3,4-Dihydro-1H-isoquinoline-2.6-dicarboxylic acid 2-tert-butyl ester-6-methyl ester

di-tert-butyl dicarbonate

6-hydroxy-1,2,3,4-tetrahydroisoquinoline hydrochloride

N-tert-butoxycarbonyl-6-hydroxy-1,2,3,4-tetrahydroisoquinoline

Downstream raw materials:

3-(4-(2-(cyclopropylsulfonyl)-1,2,3,4-tetrahydroisoquinolin-6-ylamino)-5-methylpyrimidin-2-ylamino)benzenesulfonamide

3-(4-(2-(2-chloroacetyl)-1,2,3,4-tetrahydroisoquinolin-6-ylamino)-5-methylpyrimidin-2-ylamino)benzenesulfonamide

C₂₀H₂₂N₆O₂S

tert-butyl 6-amino-3,4-dihydroisoquinoline-2(1H)-carboxylate

Refernces

• 1、 -. "INHIBITORS OF MLH1 AND/OR PMS2 FOR CANCER TREATMENT". Paragraph 00503-00504. . Retrieved 2021/12/28.
• 2、 Shao, Jingwei,Zhu, Kongkai,Du, Daohai,Zhang, Yuanyuan,Tao, Hongrui,Chen, Zhifeng,Jiang, Hualiang,Chen, Kaixian,Luo, Cheng,Duan, Wenhu. "Discovery of 2-substituted-N-(3-(3,4-dihydroisoquinolin-2(1H)-yl)-2-hydroxypropyl)-1,2,3,4-tetrahydroisoquinoline-6-carboxamide as potent and selective protein arginine methyltransferases 5 inhibitors: Design, synthesis and biological evaluation". . p. 317 - 333. Retrieved 2019/01/04.