(S)-2-(((S)-1-Ethoxy-1-oxo-4-phenylbutan-2-yl)amino)-6-(2,2,2-trifluoroacetamido)hexanoic acid

Base Information

• Chemical Name: (S)-2-(((S)-1-Ethoxy-1-oxo-4-phenylbutan-2-yl)amino)-6-(2,2,2-trifluoroacetamido)hexanoic acid
• CAS No.: 116169-90-5
• Molecular Formula: C20H27F3N2O5
• Molecular Weight: 432.44
• European Community (EC) Number: 601-412-9
• DSSTox Substance ID: DTXSID50437842
• Nikkaji Number: J319.654B
• Mol file: 116169-90-5.mol

Synonyms:116169-90-5;(S)-2-(((S)-1-Ethoxy-1-oxo-4-phenylbutan-2-yl)amino)-6-(2,2,2-trifluoroacetamido)hexanoic acid;N2-(1S-Ethoxycarbonyl-3-phenylpropyl)-N6-trifluoroacetyl-L-lysine;(2S)-2-[[(2S)-1-ethoxy-1-oxo-4-phenylbutan-2-yl]amino]-6-[(2,2,2-trifluoroacetyl)amino]hexanoic acid;N2-(S)-1-Ethoxycarbonyl-3-phenylpropyl-N8-trifluoroacetyl-L-lysine;N2-[(1S)-Ethoxycarbonyl-3-phenylpropyl]-N6-Trifluoroacetyl-L-Lysine;N2-(1-(S)-Ethoxycarbonyl-3-Phenylpropyl)-N6-Trifluoroacetyl-L-Lysine;N2-[(1S)-Ethoxycarbony1-3-phenylpropyl]-N6-trifluoroacetyl-L-lysine;N2-[1-(S)-ethoxycarbonyl-3-phenylpropyl]-N6-trifluoroacetyl-L-lysine;C20H27F3N2O5;SCHEMBL901542;DTXSID50437842;MFCD06658211;AKOS015888707;AC-6229;AS-15712;CS-0186155;E77203;A803567;J-005805;N2-[(S)-1-ethoxycarbonyl-3-phenylpropyl]-N6-trifluoroacetyl-L-lysine;N~2~-[(2S)-1-Ethoxy-1-oxo-4-phenylbutan-2-yl]-N~6~-(trifluoroacetyl)-L-lysine;(2S)-2-[[(1S)-1-ethoxycarbonyl-3-phenyl-propyl]amino]-6-[(2,2,2-trifluoroacetyl)amino]hexanoic acid;(2S)-2-{[(2S)-1-ETHOXY-1-OXO-4-PHENYLBUTAN-2-YL]AMINO}-6-(2,2,2-TRIFLUOROACETAMIDO)HEXANOIC ACID;(2S)-2-{[(2S)-1-ethoxy-1-oxo-4-phenylbutan-2-yl]amino}-6-(trifluoroacetamido)hexanoic acid;(S)-2-(((S)-1-Ethoxy-1-oxo-4-phenylbutan-2-yl)amino)-6-(2,2,2-trifluoroacetamido)hexanoicacid;(S)-2-((S)-1-ethoxy-1-oxo-4-phenylbutan-2-ylamino)-6-(2,2,2-trifluoroacetamido)hexanoic acid;Benzenebutanoic acid, alpha-[[(1S)-1-carboxy-5-[(2,2,2-trifluoroacetyl)amino]pentyl]amino]-, 1-ethyl ester, (alphaS)-

Chemical Property of (S)-2-(((S)-1-Ethoxy-1-oxo-4-phenylbutan-2-yl)amino)-6-(2,2,2-trifluoroacetamido)hexanoic acid

Chemical Property:

• Appearance/Colour: White solid
• Melting Point: 134-136 °C
• Refractive Index: 1.495
• Boiling Point: 586.987 °C at 760 mmHg
• PKA: 2.25±0.24(Predicted)
• Flash Point: 308.799 °C
• PSA: 104.73000
• Density: 1.234 g/cm³
• LogP: 3.22430
• Storage Temp.: -20?C Freezer
• Solubility.: DMSO, Methanol
• XLogP3: 1.3
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 9
• Rotatable Bond Count: 14
• Exact Mass: 432.18720645
• Heavy Atom Count: 30
• Complexity: 551

Purity/Quality:

99% ^*data from raw suppliers

N2-(S)-1-Ethoxycarbonyl-3-phenylpropyl-N8-trifluoroacetyl-L-lysine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCOC(=O)C(CCC1=CC=CC=C1)NC(CCCCNC(=O)C(F)(F)F)C(=O)O
• Isomeric SMILES: CCOC(=O)[C@H](CCC1=CC=CC=C1)N[C@@H](CCCCNC(=O)C(F)(F)F)C(=O)O
• Uses: Lisinopryl intermediate Lisinopryl intermediate.

Technology Process of (S)-2-(((S)-1-Ethoxy-1-oxo-4-phenylbutan-2-yl)amino)-6-(2,2,2-trifluoroacetamido)hexanoic acid

There total 5 articles about (S)-2-(((S)-1-Ethoxy-1-oxo-4-phenylbutan-2-yl)amino)-6-(2,2,2-trifluoroacetamido)hexanoic 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: 94.0%

→ N2-(1(S)-ethoxycarbonyl-3-cyclohexylpropyl)-N6-trifluoroacetyl-L-lysine (488760-32-3) + N2-(1(R)-ethoxycarbonyl-3-phenylpropyl)-N6-trifluoroacetyl-L-lysine (130414-30-1) + N2-[1-(S)-ethoxycarbonyl-3-phenylpropyl]-N6-trifluoroacetyl-L-lysine (116169-90-5)

Guidance literature:

Purification / work up;

Reference yield: 86.0%

C8H12F3N2O3(1-)*C4H12N(1+) + ethyl (R)-2-hydroxy-4-phenylbutyrate (90315-82-5) → N2-[1-(S)-ethoxycarbonyl-3-phenylpropyl]-N6-trifluoroacetyl-L-lysine (116169-90-5)

Guidance literature:

ethyl (R)-2-hydroxy-4-phenylbutyrate; With sodium carbonate; p-toluenesulfonyl chloride; In dichloromethane; at 0 - 25 ℃; for 8h;

C₈H₁₂F₃N₂O₃^(1-)*C₄H₁₂N⁽¹⁺⁾; In dichloromethane; at 15 ℃; for 10h;

Reference yield: 84.7%

C8H12F3N2O3(1-)*Na(1+) + ethyl (R)-2-hydroxy-4-phenylbutyrate (90315-82-5) → N2-[1-(S)-ethoxycarbonyl-3-phenylpropyl]-N6-trifluoroacetyl-L-lysine (116169-90-5)

Guidance literature:

ethyl (R)-2-hydroxy-4-phenylbutyrate; With pyridine; methanesulfonyl chloride; In tetrahydrofuran; at 0 - 35 ℃; for 6h;

C₈H₁₂F₃N₂O₃^(1-)*Na⁽¹⁺⁾; In tetrahydrofuran; at 25 ℃; for 10h;

upstream raw materials:

ethyl (R)-2-hydroxy-4-phenylbutyrate

Downstream raw materials:

N^ε-(trifluoroacetyl)-N^α-<(S)-1-(ethoxycarbonyl)-3-phenylpropyl>-L-lysyl-L-proline

Refernces

• 1、 -. "METHOD FOR PURIFYING N2-(1(S)-ETHOXYCARBONYL-3-PHENYLPROPYL)-N6-TRIFLUOROACETYL-L-LYSINE". Page 8-17. . Retrieved 2008/06/13.