(S)-2-(((Benzyloxy)carbonyl)amino)-3-cyclohexylpropanoic acid

Base Information

• Chemical Name: (S)-2-(((Benzyloxy)carbonyl)amino)-3-cyclohexylpropanoic acid
• CAS No.: 25341-42-8
• Molecular Formula: C17H23 N O4
• Molecular Weight: 305.374
• Hs Code.: 2924299090
• DSSTox Substance ID: DTXSID50556769
• Nikkaji Number: J2.297.262F
• Mol file: 25341-42-8.mol

Synonyms:25341-42-8;Z-Cha-OH;(S)-2-(((Benzyloxy)carbonyl)amino)-3-cyclohexylpropanoic acid;Z-3-cyclohexyl-L-alanine;cbz-3-cyclohexyl-l-alanine;(2S)-3-cyclohexyl-2-(phenylmethoxycarbonylamino)propanoic acid;MFCD00191081;(2S)-2-{[(BENZYLOXY)CARBONYL]AMINO}-3-CYCLOHEXYLPROPANOIC ACID;Z-L-Cha-OH;Z-beta-cyclohexyl-L-alanine;N-Benzyloxycarbonyl-L-3-cyclohexylalanine;Z-Cha-OH DHCA salt;Z-L-Cha-OH DHCA salt;SCHEMBL4622697;DTXSID50556769;MNABZONTQXNLDT-HNNXBMFYSA-N;CBZ-L-3-CYCLOHEXYL ALANINE;Z-Cha-OH dicyclohexylammonium salt;Z-3-cyclohexyl-L-alanine DHCA salt;AKOS015911046;N-Benzyloxycarbonyl-3-cyclohexylalanine;Z-beta-cyclohexyl-L-alanine DHCA salt;Z-Cha-OH, >=95.0% (HPLC);DS-18391;CS-0103659;F14549;EN300-1670923;N-[(Benzyloxy)carbonyl]-3-cyclohexyl-L-alanine;A851230;J-300443;2(S)-benzyloxycarbonylamino-3-cyclohexylpropionic acid;(S)-2-Benzyloxycarbonylamino-3-cyclohexyl-propionic acid;(S)-2-benzyloxycarbonylaMino-3-cyclohexylpropanoic acid;3-cyclohexyl-N-{[(phenylmethyl)oxy]carbonyl}-L-alanine;(S)-2-(benzyloxycarbonylamino)-3-cyclohexylpropanoic acid;N-(Benzyloxycarbonyl)-2(S)-amino-3-cyclohexylpropionic acid;N-alpha-BenZyloxycarbonyl-L-cyclohexylalanine (CbZ-L-Cha-OH)

Chemical Property of (S)-2-(((Benzyloxy)carbonyl)amino)-3-cyclohexylpropanoic acid

Chemical Property:

• Boiling Point: 501.4±43.0 °C(Predicted)
• PKA: 4.00±0.10(Predicted)
• PSA: 75.63000
• Density: 1.167
• LogP: 3.72730
• Storage Temp.: 2-8°C
• XLogP3: 4.2
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 7
• Exact Mass: 305.16270821
• Heavy Atom Count: 22
• Complexity: 360

Purity/Quality:

98%,99%, ^*data from raw suppliers

(S)-2-(((Benzyloxy)carbonyl)amino)-3-cyclohexylpropanoicAcid ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1CCC(CC1)CC(C(=O)O)NC(=O)OCC2=CC=CC=C2
• Isomeric SMILES: C1CCC(CC1)C[C@@H](C(=O)O)NC(=O)OCC2=CC=CC=C2

Technology Process of (S)-2-(((Benzyloxy)carbonyl)amino)-3-cyclohexylpropanoic acid

There total 10 articles about (S)-2-(((Benzyloxy)carbonyl)amino)-3-cyclohexylpropanoic 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: 95.0%

L-cyclohexylalanine (27527-05-5) + benzyl chloroformate (501-53-1,94274-21-2) → (S)-2-benzyloxycarbonylamino-3-cyclohexylpropionic acid (25341-42-8)

Guidance literature:

With potassium carbonate; In tetrahydrofuran; water; at 0 - 20 ℃;

Reference yield:

β-cyclohexylalanine (4441-50-3,27527-05-5,55658-63-4,58717-02-5) + benzyl chloroformate (501-53-1,94274-21-2) → (S)-2-benzyloxycarbonylamino-3-cyclohexylpropionic acid (25341-42-8)

Guidance literature:

With hydrogenchloride; In 1,4-dioxane; sodium hydroxide; diethyl ether; water; ethyl acetate;

Reference yield:

methyl 3-cyclohexyl-L-alaninate hydrochloride (17193-39-4,144644-00-8) → (S)-2-benzyloxycarbonylamino-3-cyclohexylpropionic acid (25341-42-8)

Guidance literature:

Multi-step reaction with 3 steps

1: 1,4-dioxane

2: triethylamine

3: lithium hydroxide; water / tetrahydrofuran

With water; triethylamine; lithium hydroxide; In tetrahydrofuran; 1,4-dioxane;

DOI:10.1016/j.bmcl.2012.11.026

upstream raw materials:

(2S,4S)-4-(cyclohexylmethyl)-2-(1,1-dimethylethyl)-5-oxo-3-oxazolidinecarboxylic acid phenylmethyl ester

Cyclohexyl iodide

benzyl (2S,4S)-2-(tert-butyl)-4-isobutyl-5-oxooxazolidine-3-carboxylate

β-cyclohexylalanine

Downstream raw materials:

L-cyclohexylalanine

C₂₅H₃₅N₃O₆

C₂₄H₃₅N₃O₅

benzyl ((S)-3-cyclohexyl-1-oxo-1-(((S)-1-oxo-3-(2-oxopyrrolidin-3-yl)propan-2-yl)amino)propan-2-yl)carbamate

Refernces

• 1、 Mandadapu, Sivakoteswara Rao,Gunnam, Mallikarjuna Reddy,Tiew, Kok-Chuan,Uy, Roxanne Adeline Z.,Prior, Allan M.,Alliston, Kevin R.,Hua, Duy H.,Kim, Yunjeong,Chang, Kyeong-Ok,Groutas, William C.. "Inhibition of norovirus 3CL protease by bisulfite adducts of transition state inhibitors". . p. 62 - 65. Retrieved 2013/02/23.
• 2、 -. "ACYCLIC 1,3-DIAMINES AND USES THEREFOR". Page/Page column 47. . Retrieved 2010/10/20.