4-[2-Methoxycarbonyl-2-(BOC-amino)ethyl]phenylboronic acid pinacol ester

Base Information

• Chemical Name: 4-[2-Methoxycarbonyl-2-(BOC-amino)ethyl]phenylboronic acid pinacol ester
• CAS No.: 220587-29-1
• Molecular Formula: C21H32BNO6
• Molecular Weight: 405.299
• European Community (EC) Number: 889-129-9
• Mol file: 220587-29-1.mol

Synonyms:335030-22-3;4-[2-Methoxycarbonyl-2-(BOC-amino)ethyl]phenylboronic acid pinacol ester;220587-29-1;methyl 2-[(2-methylpropan-2-yl)oxycarbonylamino]-3-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]propanoate;SCHEMBL539840;(s)-methyl 2-(tert-butoxycarbonylamino)-3-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)propanoate;BCP19729;AB88468;AB89340;AT29520;SB17957;BS-28491;CS-0174677;4-[2-Methoxycarbonyl-2-(BOC-amino)ethyl]phenylboronicacidpinacolester;Methyl 2-((tert-butoxycarbonyl)amino)-3-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)propanoate

Chemical Property of 4-[2-Methoxycarbonyl-2-(BOC-amino)ethyl]phenylboronic acid pinacol ester

Chemical Property:

• Boiling Point: 521.897 °C at 760 mmHg
• PKA: 10.96±0.46(Predicted)
• Flash Point: 269.434 °C
• PSA: 86.58000
• Density: 1.109 g/cm³
• LogP: 2.79900
• Storage Temp.: 2-8°C
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 8
• Exact Mass: 405.2322679
• Heavy Atom Count: 29
• Complexity: 577

Purity/Quality:

99% ^*data from raw suppliers

(S)-Methyl2-((tert-butoxycarbonyl)amino)-3-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)propanoate 95+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: B1(OC(C(O1)(C)C)(C)C)C2=CC=C(C=C2)CC(C(=O)OC)NC(=O)OC(C)(C)C

Technology Process of 4-[2-Methoxycarbonyl-2-(BOC-amino)ethyl]phenylboronic acid pinacol ester

There total 20 articles about 4-[2-Methoxycarbonyl-2-(BOC-amino)ethyl]phenylboronic acid pinacol ester 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: 100.0%

methyl N-(tert-butoxycarbonyl)-O-[(trifluoromethyl)sulfonyl]-L-tyrosinate (112766-18-4) + bis(pinacol)diborane (73183-34-3) → methyl (S)-2-((tert-butoxycarbonyl)amino)-3-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)propanoate (220587-29-1,335030-24-5)

Guidance literature:

With potassium acetate; palladium diacetate; tricyclohexylphosphine; In acetonitrile; for 5h; Reflux; Large scale;

DOI:10.1021/acs.oprd.9b00520

Reference yield: 100.0%

bis(pinacol)diborane (73183-34-3) + (S)-3-(4-Bromo-phenyl)-2-tert-butoxycarbonylamino-propionic acid methyl ester (266306-18-7) → methyl (S)-2-((tert-butoxycarbonyl)amino)-3-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)propanoate (220587-29-1,335030-24-5)

Guidance literature:

With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate; In 1,4-dioxane; at 90 ℃; Inert atmosphere; Sealed tube;

Reference yield: 94.0%

methyl N-(tert-butoxycarbonyl)-O-[(trifluoromethyl)sulfonyl]-L-tyrosinate (112766-18-4) + 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane (25015-63-8) → methyl (S)-2-((tert-butoxycarbonyl)amino)-3-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)propanoate (220587-29-1,335030-24-5)

Guidance literature:

With 4-methyl-morpholine; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; In 1,4-dioxane; dichloromethane; at 80 ℃; for 24h; Inert atmosphere;

DOI:10.1016/j.tetlet.2010.01.006

upstream raw materials:

methyl N-(tert-butoxycarbonyl)-O-[(trifluoromethyl)sulfonyl]-L-tyrosinate

N-(tert-butoxycarbonyl)-4-iodo-L-phenylalanine methyl ester

4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane

bis(pinacol)diborane

Downstream raw materials:

(S)-methyl 2-(tert-butoxycarbonylamino)-3-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)propanoate

(2S)-{4-[2-tert-butoxycarbonylamino-2-(methoxycarbonyl)-ethyl]-phenyl}difluoromethyl-phosphonic acid diethyl ester

(S)-(4-(2-((tert-butoxycarbonyl)amino)-3-methoxy-3-oxopropyl)phenyl)boronic acid

methyl N-(tert-butoxycarbonyl)-4-(3-methyl-2,6-dioxo-3,6-dihydropyrimidine-1(2H)-yl)-L-phenylalaninate

Refernces

• 1、 Das, Mowpriya,Glorius, Frank,Maisuls, Iván,Strassert, Cristian A.,Tan, Guangying. "Rhodium-Catalyzed Dealkenylative Arylation of Alkenes with Arylboronic Compounds". supporting information. p. 15650 - 15655. Retrieved 2021/06/08.
• 2、 Bednarz, Mark S.,Iimura, Shinya,Kanamarlapudi, Ramanaiah C.,Lim, Ngiap-Kie,Wu, Wenxue,Yan, Jie,Zhang, Haiming,Zhao, Matthew M.. "Process Development of Tryptophan Hydroxylase Inhibitor LX1031, a Drug Candidate for the Treatment of Irritable Bowel Syndrome". . p. 261 - 273. Retrieved 2020/03/10.