Boc-3-cyano-L-phenylalanine

Base Information

• Chemical Name: Boc-3-cyano-L-phenylalanine
• CAS No.: 131980-30-8
• Molecular Formula: C15H18N2O4
• Molecular Weight: 290.319
• Hs Code.: 29223900
• DSSTox Substance ID: DTXSID20370338
• Wikidata: Q72448967
• Mol file: 131980-30-8.mol

Synonyms:131980-30-8;Boc-Phe(3-CN)-OH;Boc-3-cyano-L-phenylalanine;Boc-L-3-Cyanophenylalanine;(S)-2-((tert-Butoxycarbonyl)amino)-3-(3-cyanophenyl)propanoic acid;(2S)-3-(3-cyanophenyl)-2-[(2-methylpropan-2-yl)oxycarbonylamino]propanoic acid;(2S)-2-{[(tert-butoxy)carbonyl]amino}-3-(3-cyanophenyl)propanoic acid;SCHEMBL3748882;Boc-3-cyano-(L)-phenylalanine;DTXSID20370338;FDQDHMZKOPOWFE-LBPRGKRZSA-N;MFCD00797560;AKOS015836513;AKOS015889803;AC-9889;AM82767;CS-W012195;TS-01053;N-t-Butoxycarbonyl-3-cyano-(S)-phenylalanine;A50145;Boc-Phe(3-CN)-OH, >=98.0% (TLC);(S)N-t-butoxycarbonyl-3-(3-cyanophenyl)alanine;EN300-7368635;J-006100;L-Phenylalanine, 3-cyano-N-[(1,1-dimethylethoxy)carbonyl]-;(S)-2-(tert-butoxycarbonylamino)-3-(3-cyanophenyl)propanoic acid

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

Chemical Property:

• Appearance/Colour: off-white to light yellow crystalline powder
• Vapor Pressure: 3.09E-10mmHg at 25°C
• Melting Point: 124.1 °C
• Refractive Index: 1.548
• Boiling Point: 485.4 °C at 760 mmHg
• PKA: 3.75±0.10(Predicted)
• Flash Point: 247.4 °C
• Density: 1.22 g/cm³
• Storage Temp.: Store at 0°C
• XLogP3: 2.2
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 6
• Exact Mass: 290.12665706
• Heavy Atom Count: 21
• Complexity: 433

Purity/Quality:

99% ^*data from raw suppliers

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

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 20/21/22
• Safety Statements: 36/37

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

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

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

There total 7 articles about Boc-3-cyano-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: 85.0%

di-tert-butyl dicarbonate (24424-99-5) + 3-cyano-(D,L)-phenylalanine (57213-48-6) → (S)-2-((tert-butoxycarbonyl)amino)-3-(3-cyanophenyl)propanoic acid (131980-30-8)

Guidance literature:

di-tert-butyl dicarbonate; 3-cyano-(D,L)-phenylalanine; With triethylamine; In methanol; at 25 ℃;

With hydrogenchloride; water; In ethyl acetate; for 0.5h;

Reference yield: 50.0%

Phe(3-CN)-OH*HCl + di-tert-butyl dicarbonate (24424-99-5) → (S)-2-((tert-butoxycarbonyl)amino)-3-(3-cyanophenyl)propanoic acid (131980-30-8)

Guidance literature:

With sodium hydroxide; In 1,4-dioxane; water; at 0 - 20 ℃; pH=8 - 9;

DOI:10.1021/jm2011996

Reference yield:

NaCl-saturated water + Boc pyrocarbonate + 3-cyano-(D,L)-phenylalanine (57213-48-6) → (S)-2-((tert-butoxycarbonyl)amino)-3-(3-cyanophenyl)propanoic acid (131980-30-8)

Guidance literature:

With sodium hydroxide; In 1,4-dioxane; potassium hydrogensulfate; ethyl acetate;

upstream raw materials:

di-tert-butyl dicarbonate

3-cyano-(D,L)-phenylalanine

2-(tert-butoxycarbonyloxyimino)-2-phenylacetonitrile

Refernces

• 1、 Saupe, Sebastian M.,Steinmetzer, Torsten. "A new strategy for the development of highly potent and selective plasmin inhibitors". supporting information; experimental part. p. 1171 - 1180. Retrieved 2012/04/17.
• 2、 -. "METHOD FOR CLEANING 3-HYDROXYAMIDINOPHENYLALANINE DERIVATIVES BY THE PRECIPITATION AND RECRYSTALLISATION OF A SALT AND AN AROMATIC SULPHONIC ACID". Page/Page column 12. . Retrieved 2008/06/13.