(R)-Methyl 2-Boc-amino-3-(4-iodophenyl)propionate

Base Information

• Chemical Name: (R)-Methyl 2-Boc-amino-3-(4-iodophenyl)propionate
• CAS No.: 210962-91-7
• Molecular Formula: C₁₅H₂₀INO₄
• Molecular Weight: 405.233
• DSSTox Substance ID: DTXSID40707400
• Wikidata: Q82641189
• Mol file: 210962-91-7.mol

Synonyms:210962-91-7;(R)-Methyl 2-Boc-amino-3-(4-iodophenyl)propionate;(R)-Methyl 2-((tert-butoxycarbonyl)amino)-3-(4-iodophenyl)propanoate;methyl (2R)-3-(4-iodophenyl)-2-[(2-methylpropan-2-yl)oxycarbonylamino]propanoate;Boc-4-iodo-D-phenylalanine methyl ester;Methyl (R)-2-((tert-butoxycarbonyl)amino)-3-(4-iodophenyl)propanoate;DTXSID40707400;HNCUXLSIVYDGBW-GFCCVEGCSA-N;MFCD14580868;D-Phenylalanine, N-[(1,1-dimethylethoxy)carbonyl]-4-iodo-, methyl ester;AS-37978;CS-0067783;Methyl N-(tert-butoxycarbonyl)-4-iodo-D-phenylalaninate;methyl (2r)-2-t-butoxycarbonylamino-3-(4-iodophenyl)propionate;methyl (2R)-t-butoxycarbonylamino-3-(4-iodophenyl)propionate;(R)-Methyl2-((tert-butoxycarbonyl)amino)-3-(4-iodophenyl)propanoate;(s)-2-tert-butoxycarbonylamino-3-(4-iodo-phenyl)-propionic acid methyl ester

Chemical Property of (R)-Methyl 2-Boc-amino-3-(4-iodophenyl)propionate

Chemical Property:

• PSA: 64.63000
• LogP: 4.09290
• XLogP3: 3
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 7
• Exact Mass: 405.04371
• Heavy Atom Count: 21
• Complexity: 359

Purity/Quality:

98.5% ^*data from raw suppliers

(R)-Methyl2-((tert-butoxycarbonyl)amino)-3-(4-iodophenyl)propanoate 95+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CC(C)(C)OC(=O)NC(CC1=CC=C(C=C1)I)C(=O)OC
• Isomeric SMILES: CC(C)(C)OC(=O)N[C@H](CC1=CC=C(C=C1)I)C(=O)OC

Technology Process of (R)-Methyl 2-Boc-amino-3-(4-iodophenyl)propionate

There total 22 articles about (R)-Methyl 2-Boc-amino-3-(4-iodophenyl)propionate 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%

N-Boc-4-I-Phe-OH (103882-09-3,62129-44-6) + methyl iodide (74-88-4) → N-(tert-butoxycarbonyl)-4-iodo-L-phenylalanine methyl ester (113850-76-3,210962-91-7)

Guidance literature:

With sodium hydrogencarbonate; In N,N-dimethyl-formamide; at 20 ℃; for 15h;

DOI:10.1002/ejoc.201601215

Reference yield: 99.0%

methanol (67-56-1) + C9H9ClINO + di-tert-butyl dicarbonate (24424-99-5) → N-(tert-butoxycarbonyl)-4-iodo-L-phenylalanine methyl ester (113850-76-3,210962-91-7)

Guidance literature:

With sodium hydrogencarbonate; In tetrahydrofuran;

DOI:10.1016/j.bmcl.2012.01.037

Reference yield: 98.0%

methyl iodide (74-88-4) → N-tert-butyloxycarbonyl-(L)4-iodophenylalanine methyl ester (796072-33-8,210962-91-7)

Guidance literature:

N-Boc-DL-4-iodophenylalanine; With potassium carbonate; In N,N-dimethyl-formamide; for 0.25h;

methyl iodide; In N,N-dimethyl-formamide; at 0 - 20 ℃; for 16h;

upstream raw materials:

di-tert-butyl dicarbonate

(S)-methyl 2-amino-3-(4-iodophenyl)propanoate

diazomethane

N-Boc-4-I-Phe-OH

Downstream raw materials:

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

methyl (R)-2-((tert-butoxycarbonyl)amino)-3-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)propanoate

N-(4-pentenoyl)-4[(4’;1’,1”)biphenyl]-L-phenylalanine pdCpA ester

((4-methoxyphenyl)((4-(S)-2-(di-tert-butoxycarbonyl)amino)-3-oxo-3-methoxypropyl)phenyl)(trifluoromethanesulfonyl)-λ³-iodane

Refernces

• 1、 -. "Preparation method of sacubitril intermediate". Paragraph 0043-0044; 0046-0047. . Retrieved 2021/04/17.
• 2、 Hutton, Craig A.,Shabani, Sadegh. "Total Synthesis of Seongsanamide B". supporting information. . Retrieved 2020/06/05.