3-(4-iodophenyl)-2-[(2-methylpropan-2-yl)oxycarbonylamino]propanoic Acid

Base Information

• Chemical Name: 3-(4-iodophenyl)-2-[(2-methylpropan-2-yl)oxycarbonylamino]propanoic Acid
• CAS No.: 62129-44-6
• Molecular Formula: C₁₄H₁₈INO₄
• Molecular Weight: 391.206
• Hs Code.: 2924299090
• European Community (EC) Number: 873-148-4
• Mol file: 62129-44-6.mol

Synonyms:103882-09-3;Boc-p-iodo-DL-Phe-OH;Boc-DL-Phe(4-I)-OH;3-(4-iodophenyl)-2-[(2-methylpropan-2-yl)oxycarbonylamino]propanoic Acid;Boc-4-iodo-DL-phenylalanine;Boc-4'-iodo-D-Phe;Boc-p-iodo-D-Phe-OH;n-boc-4-iodo-l-phenylalanine;2-(tert-butoxycarbonylamino)-3-(4-iodophenyl)propanoic acid;MFCD00037119;MFCD00079670;N-Boc-4-Iodo-DL-phenylalanine;BOC-4-IODO PHENYLALANINE;Boc-D-4-Iodophe;Boc-4-Iodo-Phe-OH;SCHEMBL1201951;JZLZDBGQWRBTHN-UHFFFAOYSA-N;MFCD00176869;AKOS009157234;SY014865;SY101866;FT-0640808;FT-0642546;FT-0643706;F79076;EN300-1299481;2-tert-butoxycarbonylamino-3-(4-iodophenyl)-propanoic acid;2-{[(tert-butoxy)carbonyl]amino}-3-(4-iodophenyl)propanoic acid

Chemical Property of 3-(4-iodophenyl)-2-[(2-methylpropan-2-yl)oxycarbonylamino]propanoic Acid

Chemical Property:

• Appearance/Colour: White powder
• Melting Point: ~150°C (dec.)
• Boiling Point: 475.3 °C at 760 mmHg
• PKA: 3.84±0.10(Predicted)
• Flash Point: 241.3 °C
• PSA: 75.63000
• Density: 1.56 g/cm³
• LogP: 3.20250
• Storage Temp.: Store at 0°C
• Sensitive.: Light Sensitive
• Water Solubility.: Slightly soluble in water.
• XLogP3: 2.5
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 6
• Exact Mass: 391.02806
• Heavy Atom Count: 20
• Complexity: 346

Purity/Quality:

99% ^*data from raw suppliers

Boc-4-iodo-L-phenylalanine ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)(C)OC(=O)NC(CC1=CC=C(C=C1)I)C(=O)O
• Uses: N-Boc-4-iodo-L-phenylalanine is used as pharmaceutical intermediate. It is also used as a p-iodo phenyl alanine derivative with N-Boc protection.

Technology Process of 3-(4-iodophenyl)-2-[(2-methylpropan-2-yl)oxycarbonylamino]propanoic Acid

There total 9 articles about 3-(4-iodophenyl)-2-[(2-methylpropan-2-yl)oxycarbonylamino]propanoic 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: 93.0%

di-tert-butyl dicarbonate (24424-99-5) + 4-iodo-L-phenylalanine (1991-81-7,14173-41-2,24250-85-9,62561-75-5) → N-Boc-4-I-Phe-OH (103882-09-3,62129-44-6)

Guidance literature:

4-iodo-L-phenylalanine; With sodium hydroxide; In 1,4-dioxane; water; at 19 ℃;

di-tert-butyl dicarbonate; In 1,4-dioxane; water; at 0 - 30 ℃; for 8h;

Reference yield:

4-iodo-L-phenylalanine (1991-81-7,14173-41-2,24250-85-9,62561-75-5) + N-ethyl-N,N-diisopropylamine (7087-68-5) → N-Boc-4-I-Phe-OH (103882-09-3,62129-44-6)

Guidance literature:

With hydrogenchloride; sodium hydroxide; sulfuric acid; In dichloromethane; diethylene glycol dimethyl ether; ethyl acetate;

Reference yield:

L-phenylalanine (63-91-2,25191-15-5,658-69-5,67675-33-6) → N-Boc-4-I-Phe-OH (103882-09-3,62129-44-6)

Guidance literature:

Multi-step reaction with 2 steps

1.1: sodium iodate; sulfuric acid; iodine / acetic acid / 18 h / 70 °C

1.2: 0.5 h / 70 °C

2.1: sodium hydroxide / tert-butyl alcohol / 18 h / 20 °C

With sodium iodate; sulfuric acid; iodine; sodium hydroxide; In acetic acid; tert-butyl alcohol;

DOI:10.1021/ja209352s

upstream raw materials:

di-tert-butyl dicarbonate

4-iodo-L-phenylalanine

1-bromomethyl-4-iodobenzene

diethyl tert-butoxycarbonylaminomalonate

Refernces

• 1、 Cuesta-Galisteo, Sergio,Sch?rgenhumer, Johannes,Wei, Xiaofeng,Merino, Estíbaliz,Nevado, Cristina. "Nickel-Catalyzed Asymmetric Synthesis of α-Arylbenzamides". supporting information. p. 1605 - 1609. Retrieved 2020/12/01.
• 2、 Rajput, Sunnia,McLean, Kirsty J.,Poddar, Harshwardhan,Selvam, Irwin R.,Nagalingam, Gayathri,Triccas, James A.,Levy, Colin W.,Munro, Andrew W.,Hutton, Craig A.. "Structure-Activity Relationships of cyclo(l -Tyrosyl- l -tyrosine) Derivatives Binding to Mycobacterium tuberculosis CYP121: Iodinated Analogues Promote Shift to High-Spin Adduct". supporting information. p. 9792 - 9805. Retrieved 2019/11/13.