N-Phenoxycarbonyl-L-valine

Base Information

• Chemical Name: N-Phenoxycarbonyl-L-valine
• CAS No.: 126147-70-4
• Molecular Formula: C12H15 N O4
• Molecular Weight: 237.255
• Hs Code.: 2924299090
• DSSTox Substance ID: DTXSID30431202
• Nikkaji Number: J3.259.767J
• Wikidata: Q82245027
• Mol file: 126147-70-4.mol

Synonyms:N-phenoxycarbonyl-L-valine;N-phenoxycarbonylvaline

Chemical Property of N-Phenoxycarbonyl-L-valine

Chemical Property:

• PSA: 75.63000
• LogP: 2.27510
• Storage Temp.: 2-8°C
• XLogP3: 2.5
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 5
• Exact Mass: 237.10010796
• Heavy Atom Count: 17
• Complexity: 272

Purity/Quality:

99% ^*data from raw suppliers

N-Phenoxycarbonyl-L-valine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)C(C(=O)O)NC(=O)OC1=CC=CC=C1
• Isomeric SMILES: CC(C)[C@@H](C(=O)O)NC(=O)OC1=CC=CC=C1
• Uses: N-Phenoxycarbonyl-L-valine (cas# 126147-70-4) is a compound useful in organic synthesis.

Technology Process of N-Phenoxycarbonyl-L-valine

There total 4 articles about N-Phenoxycarbonyl-L-valine 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: 100.0%

L-valine (72-18-4,25609-85-2,7004-03-7,921-10-8) + phenyl chloroformate (1885-14-9) → (2S)-3-Methyl-2-(phenoxycarbonyl)aminobutyric acid (126147-70-4)

Guidance literature:

With sodium hydroxide; potassium hydrogencarbonate; for 1.5h; Ambient temperature;

DOI:10.1055/s-1989-27337

Reference yield: 58.0%

bis(phenyl) carbonate (102-09-0) + L-valine (72-18-4,25609-85-2,7004-03-7,921-10-8) → (2S)-3-Methyl-2-(phenoxycarbonyl)aminobutyric acid (126147-70-4)

Guidance literature:

L-valine; With tetra(n-butyl)ammonium hydroxide; In methanol; at 20 ℃; for 1h;

bis(phenyl) carbonate; In acetonitrile; at 20 ℃; for 3.166h;

DOI:10.1002/pola.26775

Reference yield:

aqueous lithium hydroxide + L-valine (72-18-4,25609-85-2,7004-03-7,921-10-8) + phenyl chloroformate (1885-14-9) → (2S)-3-Methyl-2-(phenoxycarbonyl)aminobutyric acid (126147-70-4)

Guidance literature:

With lithium hydroxide; sulfuric acid; lithium chloride; In n-heptane; water; toluene;

upstream raw materials:

L-valine

phenyl chloroformate

tert-butyl methyl ether

bis(phenyl) carbonate

Downstream raw materials:

carbobenzoxy-valinyl-N-(S-acetyl)-cysteamine

L-valinyl-L-leucine

N-((N-methyl-N-((2-isopropyl-4-thiazolyl)methyl)amino)carbonyl)-L-valine methyl ester

phenyl [(2S)-3-methyl-1-{(2S)-2-[5-(4’-{2-[(2S)-1-{(2S)-3-methyl-2-[(phenoxycarbonyl)amino]butanoyl}pyrrolidin-2-yl]-1,3-thiazol-5-yl}biphenyl-4-yl)-1,3-thiazol-2-yl]pyrrolidin-1-yl}-1-oxobutan-2-yl]carbamate

Refernces

• 1、 Stoner, Eric J.,Cooper, Arthur J.,Dickman, Daniel A.,Kolaczkowski, Lawrence,Lallaman, John E.,Liu, Jih-Hua,Oliver-Shaffer, Patricia A.,Patel, Ketan M.,Paterson Jr., Joseph B.,Plata, Daniel J.,Riley, David A.,Sham, Hing L.,Stengel, Peter J.,Tien, Jien-Heh J.. "Synthesis of HIV protease inhibitor ABT-378 (lopinavir)". . p. 264 - 269. Retrieved 2000.
• 2、 -. "SPIRO COMPOUNDS AS HEPATITIS C VIRUS INHIBITORS". Paragraph 0378; 0563; 0571. . Retrieved 2015/11/09.
• 3、 Yamada, Shuhei,Koga, Koichi,Sudo, Atsushi,Goto, Mitsuaki,Endo, Takeshi. "Phosgene-free synthesis of polypeptides: Useful synthesis for hydrophobic polypeptides through polycondensation of activated urethane derivatives of α-amino acids". . p. 3726 - 3731. Retrieved 2013/09/02.