N-tert-butoxycarbonyl-N-methyl-D-homophenylalanine

Base Information

• Chemical Name: N-tert-butoxycarbonyl-N-methyl-D-homophenylalanine
• CAS No.: 1001646-83-8
• Molecular Formula: C₁₆H₂₃NO₄
• Molecular Weight: 293.363
• Mol file: 1001646-83-8.mol

Synonyms:N-tert-butoxycarbonyl-N-methyl-D-homophenylalanine

Chemical Property of N-tert-butoxycarbonyl-N-methyl-D-homophenylalanine

Chemical Property:

Purity/Quality:

95%-98% ^*data from raw suppliers

N-Boc-N-methyl-(R)-homophenylalanine 95% ee ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of N-tert-butoxycarbonyl-N-methyl-D-homophenylalanine

There total 10 articles about N-tert-butoxycarbonyl-N-methyl-D-homophenylalanine 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: 92.0%

C17H25NO2 (1404462-22-1) → N-tert-butoxycarbonyl-N-methyl-D-homophenylalanine (1001646-83-8)

Guidance literature:

With sodium periodate; ruthenium(III) trichloride hydrate; In tetrachloromethane; water; acetonitrile; for 15h; Schlenk technique; Inert atmosphere;

DOI:10.1039/c2cc36961c DOI:10.1039/c2cc36961c

Reference yield: 65.0%

(2R)-(tert-butoxycarbonylamino)-4-phenylbutanoic acid (100564-78-1,108524-68-1,142926-43-0,82732-07-8) + methyl iodide (74-88-4) → N-tert-butoxycarbonyl-N-methyl-D-homophenylalanine (1001646-83-8)

Guidance literature:

(2R)-(tert-butoxycarbonylamino)-4-phenylbutanoic acid; With sodium hydride; In tetrahydrofuran; N,N-dimethyl-formamide; at 0 ℃; for 1h; Cooling with ice;

methyl iodide; In tetrahydrofuran; N,N-dimethyl-formamide; at 0 - 20 ℃;

Reference yield:

(2R)-(tert-butoxycarbonylamino)-4-phenylbutanoic acid (100564-78-1,108524-68-1,142926-43-0,82732-07-8) + dimethyl sulfate (77-78-1) → N-tert-butoxycarbonyl-N-methyl-D-homophenylalanine (1001646-83-8)

Guidance literature:

(2R)-(tert-butoxycarbonylamino)-4-phenylbutanoic acid; dimethyl sulfate; With water; sodium hydride; In tetrahydrofuran; mineral oil; at 20 ℃; for 2.83333h;

In tetrahydrofuran; water; mineral oil; at 20 ℃; for 1.16667h;

upstream raw materials:

(2R)-(tert-butoxycarbonylamino)-4-phenylbutanoic acid

dimethyl sulfate

5-phenylpent-1-en-3-yl 2,2,2-trichloroacetimidate

N-(4-methoxyphenyl)-N-methyl-[1-(2-phenylethyl)prop-2-en-1-yl]amine

Downstream raw materials:

(2S,4R)-4-(2-Aminoacetamido)-N-methyl-N-[(1R)-3-phenyl-1-(3-quinolylcarbamoyl)propyl]-2-pyrrolidinecarboxamide

Refernces

• 1、 Arnold, Jeffrey S.,Nguyen, Hien M.. "Rhodium-catalyzed asymmetric amination of allylic trichloroacetimidates". . p. 2101 - 2108. Retrieved 2013/08/23.
• 2、 Arnold, Jeffrey S.,Cizio, Gregory T.,Heitz, Drew R.,Nguyen, Hien M.. "Rhodium-catalyzed regio- and enantioselective amination of racemic secondary allylic trichloroacetimidates with N-methyl anilines". . p. 11531 - 11533. Retrieved 2013/01/15.