4-Cyclohexyl-2-hydroxy-3-(3-methylsulfanyl-2-(2-((morpholine-4-carbonyl)amino)-3-phenylpropionylamino)propionylamino)butyric acid

Base Information

• Chemical Name: 4-Cyclohexyl-2-hydroxy-3-(3-methylsulfanyl-2-(2-((morpholine-4-carbonyl)amino)-3-phenylpropionylamino)propionylamino)butyric acid
• CAS No.: 114457-62-4
• Molecular Formula: C14H18 N2 O4
• Molecular Weight: 278.308
• DSSTox Substance ID: DTXSID20150738
• Nikkaji Number: J887.969I
• Wikidata: Q83016927
• ChEMBL ID: CHEMBL1611487
• Mol file: 114457-62-4.mol

Synonyms:4-cyclohexyl-2-hydroxy-3-(3-methylsulfanyl-2-(2-((morpholine-4-carbonyl)amino)-3-phenylpropionylamino)propionylamino)butyric acid;CP 84,364;CP 84364;CP-84,864;CP-84364

Chemical Property of 4-Cyclohexyl-2-hydroxy-3-(3-methylsulfanyl-2-(2-((morpholine-4-carbonyl)amino)-3-phenylpropionylamino)propionylamino)butyric acid

Chemical Property:

• Vapor Pressure: 1.97E-13mmHg at 25°C
• Boiling Point: 561.2°Cat760mmHg
• Flash Point: 293.2°C
• Density: 1.28g/cm³
• XLogP3: 0.8
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 4
• Exact Mass: 278.12665706
• Heavy Atom Count: 20
• Complexity: 336

Purity/Quality:

98% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1COCCN1C(=O)NC(CC2=CC=CC=C2)C(=O)O
• Isomeric SMILES: C1COCCN1C(=O)N[C@@H](CC2=CC=CC=C2)C(=O)O

Technology Process of 4-Cyclohexyl-2-hydroxy-3-(3-methylsulfanyl-2-(2-((morpholine-4-carbonyl)amino)-3-phenylpropionylamino)propionylamino)butyric acid

There total 12 articles about 4-Cyclohexyl-2-hydroxy-3-(3-methylsulfanyl-2-(2-((morpholine-4-carbonyl)amino)-3-phenylpropionylamino)propionylamino)butyric 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: 76.5%

(S)-methyl 2-(morpholine-4-carboxamido)-3-phenylpropanoate (114473-20-0) → Nα-(4-morpholinecarbonyl)-L-phenylalanine (114457-62-4)

Guidance literature:

(S)-methyl 2-(morpholine-4-carboxamido)-3-phenylpropanoate; With sodium hydroxide; In methanol; for 4h;

With hydrogenchloride; In water; pH=2;

DOI:10.3109/14756366.2011.651466

Reference yield:

(S)-benzyl 2-(morpholine-4-carboxamido)-3-phenylpropanoate → Nα-(4-morpholinecarbonyl)-L-phenylalanine (114457-62-4)

Guidance literature:

palladium; In methanol;

Reference yield:

methyl (2S)-2-amino-3-phenylpropanoate hydrochloride (7524-50-7) → Nα-(4-morpholinecarbonyl)-L-phenylalanine (114457-62-4)

Guidance literature:

Multi-step reaction with 3 steps

1: toluene / 90 - 100 °C

2: CH₂Cl₂ / 0.17 h / 0 - 5 °C

3: LiOH / dioxane; H₂O / 1 h / 0 - 5 °C

With lithium hydroxide; In 1,4-dioxane; dichloromethane; water; toluene;

DOI:10.1021/jm00120a006

upstream raw materials:

(S)-methyl 2-(morpholine-4-carboxamido)-3-phenylpropanoate

4-morpholinocarbonyl chloride

L-phenylalanine

methyl (2S)-2-amino-3-phenylpropanoate hydrochloride

Downstream raw materials:

N-((S)-1-oxo-3-phenyl-1-(((S,E)-5-phenyl-1-(phenylsulfonyl)pent-1-en-3-yl)amino)propan-2-yl)morpholine-4-carboxamide

phenyl (3R)-3-((N-morpholine-4-carbonyl)phenylalanyl)amino-5-phenylpent-1-enyl sulfone

phenyl (E)-3-((N-morpholine-4-carbonyl)phenylalanyl)amino-5-phenylpent-2-enyl sulfone

phenyl (Z)-3-((N-morpholine-4-carbonyl)phenylalanyl)amino-5-phenylpent-2-enyl sulfone

Refernces

• 1、 Han, Liqiang,Wen, Yanzhao,Li, Ridong,Xu, Bo,Ge, Zemei,Wang, Xin,Cheng, Tieming,Cui, Jingrong,Li, Runtao. "Synthesis and biological activity of peptide proline-boronic acids as proteasome inhibitors". . p. 4031 - 4044. Retrieved 2017/07/05.
• 2、 Fennell, Brandon D.,Warren, Julia M.,Chung, Kevin K.,Main, Hannah L.,Arend, Andrew B.,Tochowicz, Anna,Goetz, Marion G.. "Optimization of peptidyl allyl sulfones as clan CA cysteine protease inhibitors". . p. 468 - 478. Retrieved 2013/05/21.