Boc-3-iodo-L-phenylalanine

Base Information

• Chemical Name: Boc-3-iodo-L-phenylalanine
• CAS No.: 273221-75-3
• Molecular Formula: C₁₄H₁₈INO₄
• Molecular Weight: 391.206
• Hs Code.: 2924299090
• European Community (EC) Number: 853-537-5
• DSSTox Substance ID: DTXSID20471233
• Wikidata: Q82299697
• Mol file: 273221-75-3.mol

Synonyms:Boc-3-iodo-L-phenylalanine;273221-75-3;Boc-Phe(3-I)-OH;(S)-2-((tert-Butoxycarbonyl)amino)-3-(3-iodophenyl)propanoic acid;N-Boc-3-iodo-L-phenylalanine;(2S)-3-(3-iodophenyl)-2-[(2-methylpropan-2-yl)oxycarbonylamino]propanoic Acid;(S)-2-(tert-Butoxycarbonylamino)-3-(3-iodophenyl)propanoic acid;(2S)-2-{[(tert-butoxy)carbonyl]amino}-3-(3-iodophenyl)propanoic acid;MFCD01860644;Boc-L-3-Iodophe;(S)-Boc-3-iodophenylalanine;SCHEMBL1854581;DTXSID20471233;MPTBEGFNTNOLNZ-NSHDSACASA-N;AMY22136;(2S)-2-[(tert-Butoxycarbonyl)amino]-3-(3-iodophenyl)propanoic acid;AKOS015836532;AKOS015907840;CS-13081;N-(tert-Butoxycarbonyl)-3-iodophenylalanine;CS-0154535;n-(tert-butoxycarbonyl)-3-iodo-l-phenylalanine;N12454;N-(tert-butoxycarbonyl)-3-iodo-(L)-phenylalanine;J-016733;N-alpha-t-Butyloxycarbonyl-3-iodo-L-phenylalanine (Boc-L-Phe(3-I)-OH)

Chemical Property of Boc-3-iodo-L-phenylalanine

Chemical Property:

• Boiling Point: 491.63 °C at 760 mmHg
• PKA: 3.82±0.10(Predicted)
• Flash Point: 251.129 °C
• PSA: 75.63000
• Density: 1.56 g/cm³
• LogP: 3.20250
• Storage Temp.: Store at 0°C
• XLogP3: 3.2
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 6
• Exact Mass: 391.02806
• Heavy Atom Count: 20
• Complexity: 354

Purity/Quality:

99% ^*data from raw suppliers

Boc-3-iodo-L-phenylalanine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

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

Technology Process of Boc-3-iodo-L-phenylalanine

There total 6 articles about Boc-3-iodo-L-phenylalanine 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: 67.0%

diethyl [(tert-butoxycarbonyl)amino](3-iodo-benzyl)malonate (856222-40-7) → N-(tert-butoxycarbonyl)-3-iodo-phenylalanine (273221-73-1,273221-75-3)

Guidance literature:

diethyl [(tert-butoxycarbonyl)amino](3-iodo-benzyl)malonate; With sodium hydroxide; ethanol; water; for 3h; Heating / reflux;

With hydrogenchloride; water; In ethanol; at 20 ℃; pH=~ 2;

Reference yield:

diethyl tert-butoxycarbonylaminomalonate (102831-44-7) → N-(tert-butoxycarbonyl)-3-iodo-phenylalanine (273221-73-1,273221-75-3)

Guidance literature:

Multi-step reaction with 2 steps

1.1: NaH / dimethylformamide; hexane / 2 h / 20 °C

1.2: dimethylformamide; hexane / 2 h / 20 °C

2.1: aq. AcOH / 16 h / pH 5 / Heating

With sodium hydride; acetic acid; In hexane; N,N-dimethyl-formamide;

DOI:10.1021/jm010206q

Reference yield:

m-Iodobenzyl bromide (49617-83-6) → N-(tert-butoxycarbonyl)-3-iodo-phenylalanine (273221-73-1,273221-75-3)

Guidance literature:

Multi-step reaction with 2 steps

1.1: NaH / dimethylformamide; hexane / 2 h / 20 °C

1.2: dimethylformamide; hexane / 2 h / 20 °C

2.1: aq. AcOH / 16 h / pH 5 / Heating

With sodium hydride; acetic acid; In hexane; N,N-dimethyl-formamide;

DOI:10.1021/jm010206q

upstream raw materials:

diethyl [(tert-butoxycarbonyl)amino](3-iodo-benzyl)malonate

diethyl tert-butoxycarbonylaminomalonate

m-Iodobenzyl bromide

N-(tert-butoxycarbonyl)-3-iodo-phenylalanine

Downstream raw materials:

benzyl (S)-3-([1,1’-biphenyl]-3-yl)-2-((tert-butoxycarbonyl)amino)propanoate

(S)-3-Biphenyl-3-yl-2-tert-butoxycarbonylamino-propionic acid

Refernces

• 1、 -. "Antibacterial macrocycles with substituted biphenyl". Page/Page column 20. . Retrieved 2010/11/26.