Methyl 3-(5-bromopyridin-2-YL)-2-(tert-butoxycarbonyl)propanoate

Base Information

• Chemical Name: Methyl 3-(5-bromopyridin-2-YL)-2-(tert-butoxycarbonyl)propanoate
• CAS No.: 656801-27-3
• Molecular Formula: C14H18BrNO4
• Molecular Weight: 359.22
• DSSTox Substance ID: DTXSID20701582
• Mol file: 656801-27-3.mol

Synonyms:656801-27-3;METHYL 3-(5-BROMOPYRIDIN-2-YL)-2-(TERT-BUTOXYCARBONYL)PROPANOATE;3-O-tert-butyl 1-O-methyl 2-[(5-bromopyridin-2-yl)methyl]propanedioate;DTXSID20701582;A835187;tert-Butyl methyl [(5-bromopyridin-2-yl)methyl]propanedioate;Methyl3-(5-bromopyridin-2-yl)-2-(tert-butoxycarbonyl)propanoate;O1-tert-butyl O3-methyl 2-[(5-bromo-2-pyridyl)methyl]propanedioate;2-[(5-bromo-2-pyridinyl)methyl]propanedioic acid O3-tert-butyl ester O1-methyl ester

Chemical Property of Methyl 3-(5-bromopyridin-2-YL)-2-(tert-butoxycarbonyl)propanoate

Chemical Property:

• PSA: 65.49000
• LogP: 2.51750
• XLogP3: 2.8
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 7
• Exact Mass: 343.04192
• Heavy Atom Count: 20
• Complexity: 354

Purity/Quality:

99% ^*data from raw suppliers

METHYL-3-(5-BROMOPYRIDIN-2-YL)-2-(TERT-BUTOXYCARBONYL)PROPANOATE 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)(C)OC(=O)C(CC1=NC=C(C=C1)Br)C(=O)OC

Technology Process of Methyl 3-(5-bromopyridin-2-YL)-2-(tert-butoxycarbonyl)propanoate

There total 4 articles about Methyl 3-(5-bromopyridin-2-YL)-2-(tert-butoxycarbonyl)propanoate 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: 73.0%

2,5-dibromopyridine (624-28-2) + N-(tert-butoxycarbonyl)-L-3-iodoalanine methyl ester (93267-04-0,170848-34-7,889670-02-4) → methyl (2S)-3-(5-bromopyridin-2-yl)-2-[(2-methylpropan-2-yl)oxycarbonylamino]-propanoate (656801-27-3)

Guidance literature:

N-(tert-butoxycarbonyl)-L-3-iodoalanine methyl ester; With iodine; zinc; In N,N-dimethyl-formamide; at 20 ℃; for 1h;

2,5-dibromopyridine; With bis-triphenylphosphine-palladium(II) chloride; at 68 ℃; for 2h;

DOI:10.1016/j.bmcl.2010.05.007

Reference yield: 55.0%

2,5-dibromopyridine (624-28-2) → methyl (2S)-3-(5-bromopyridin-2-yl)-2-[(2-methylpropan-2-yl)oxycarbonylamino]-propanoate (656801-27-3)

Guidance literature:

N-(tert-butoxycarbonyl)-L-3-iodoalanine methyl ester; With chloro-trimethyl-silane; ethylene dibromide; zinc; In N,N-dimethyl-formamide; at 35 - 90 ℃; for 3h;

2,5-dibromopyridine; bis-triphenylphosphine-palladium(II) chloride; In N,N-dimethyl-formamide; at 70 ℃; for 2h;

Reference yield:

N-tert-butyloxycarbonyl-L-serine methyl ester (2766-43-0) → methyl (2S)-3-(5-bromopyridin-2-yl)-2-[(2-methylpropan-2-yl)oxycarbonylamino]-propanoate (656801-27-3)

Guidance literature:

Multi-step reaction with 2 steps

1.1: triphenylphosphine; 1H-imidazole; iodine / dichloromethane / 3 h / 0 - 20 °C / Inert atmosphere

2.1: zinc; chloro-trimethyl-silane; ethylene dibromide / N,N-dimethyl-formamide / 2.5 h / 35 °C

2.2: 2 h / 70 °C

With 1H-imidazole; chloro-trimethyl-silane; iodine; ethylene dibromide; triphenylphosphine; zinc; In dichloromethane; N,N-dimethyl-formamide;

upstream raw materials:

2,5-dibromopyridine

N-(tert-butoxycarbonyl)-L-3-iodoalanine methyl ester

N-tert-butyloxycarbonyl-L-serine methyl ester

methyl (2S)-2-[N-(t-butoxycarbonyl)amino]-3-(4-methylbenzenesulfonyl)-oxypropionate

Downstream raw materials:

methyl 3-(5-aminopyridin-2-yl)-N-(tert-butoxycarbonyl)-L-alaninate

Refernces

• 1、 -. "SULFONAMIDE DERIVATIVE AND MEDICINAL USE THEREOF". Paragraph 0587-0588; 0635-0636. . Retrieved 2015/02/25.
• 2、 Germain, Herve,Harris, Craig S.,Renaud, Fabrice,Warin, Nicolas. "Efficient large-scale synthesis of Boc-L-azatyrosine". experimental part. p. 523 - 530. Retrieved 2009/06/20.