(R)-2-((((9H-Fluoren-9-yl)methoxy)carbonyl)amino)-2-cyclohexylacetic acid

Base Information

• Chemical Name: (R)-2-((((9H-Fluoren-9-yl)methoxy)carbonyl)amino)-2-cyclohexylacetic acid
• CAS No.: 198543-96-3
• Molecular Formula: C23H25NO4
• Molecular Weight: 379.45
• DSSTox Substance ID: DTXSID30426274
• Wikidata: Q72478589
• Mol file: 198543-96-3.mol

Synonyms:Fmoc-D-Chg-OH;198543-96-3;(R)-2-((((9H-Fluoren-9-yl)methoxy)carbonyl)amino)-2-cyclohexylacetic acid;Fmoc-D-Cyclohexylglycine;(2R)-2-cyclohexyl-2-(9H-fluoren-9-ylmethoxycarbonylamino)acetic acid;MFCD00190877;SCHEMBL13697519;FMOC-D-CYCLOHEXYL GLYCINE;DTXSID30426274;AKOS015911157;DS-15969;CS-0149819;(R)-alpha-(Fmoc-amino)cyclohexaneacetic acid;F14551;EN300-7414269;A851227;J-300446;N-alpha-[[(9H-Fluoren-9-yl)methoxy]carbonyl]-D-cyclohexylglycine;(2R)-2-cyclohexyl-2-{[(9H-fluoren-9-ylmethoxy)carbonyl]amino}acetic acid;(R)-2-(((9H-fluoren-9-yl)methoxy)carbonylamino)-2-cyclohexylacetic acid;N-alpha-(9-Fluorenylmethyloxycarbonyl)-D-cyclohexylglycine (Fmoc-D-Chg-OH);(2R)-2-cyclohexyl-2-({[(9H-fluoren-9-yl)methoxy]carbonyl}amino)acetic acid;Cyclohexaneacetic acid, alpha-[[(9H-fluoren-9-ylmethoxy)carbonyl]amino]-, (alphaR)-

Chemical Property of (R)-2-((((9H-Fluoren-9-yl)methoxy)carbonyl)amino)-2-cyclohexylacetic acid

Chemical Property:

• Appearance/Colour: white to off-white powder
• Melting Point: 161-187oC
• Boiling Point: 602.9±38.0 °C(Predicted)
• PKA: 3.89±0.10(Predicted)
• PSA: 75.63000
• Density: 1.238
• LogP: 4.94950
• Storage Temp.: -15°C
• XLogP3: 5.1
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 6
• Exact Mass: 379.17835828
• Heavy Atom Count: 28
• Complexity: 537

Purity/Quality:

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

Fmoc-D-2-cyclohexylglycine 99+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1CCC(CC1)C(C(=O)O)NC(=O)OCC2C3=CC=CC=C3C4=CC=CC=C24
• Isomeric SMILES: C1CCC(CC1)[C@H](C(=O)O)NC(=O)OCC2C3=CC=CC=C3C4=CC=CC=C24

Technology Process of (R)-2-((((9H-Fluoren-9-yl)methoxy)carbonyl)amino)-2-cyclohexylacetic acid

There total 3 articles about (R)-2-((((9H-Fluoren-9-yl)methoxy)carbonyl)amino)-2-cyclohexylacetic 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: 91.0%

→ C23H25NO4 (186320-22-9,161321-36-4,198543-96-3)

Guidance literature:

With chloro-trimethyl-silane; N-ethyl-N,N-diisopropylamine; In dichloromethane; for 1h; Reflux;

In dichloromethane; at 0 - 20 ℃; for 2h; Inert atmosphere;

Reference yield:

(2S)-amino(cyclohexyl)ethanoic acid (14328-51-9) + N-(9H-fluoren-2-ylmethoxycarbonyloxy)succinimide (82911-69-1) → S-(((9H-fluoren-9-yl)methoxy)carbonyl)cyclohexylglycine (161321-36-4,198543-96-3)

Guidance literature:

With sodium carbonate; In 1,4-dioxane; water; at 20 ℃; for 18h;

DOI:10.1002/anie.202017086

Reference yield:

(fluorenylmethoxy)carbonyl chloride (28920-43-6) + (2S)-amino(cyclohexyl)ethanoic acid (14328-51-9) → S-(((9H-fluoren-9-yl)methoxy)carbonyl)cyclohexylglycine (161321-36-4,198543-96-3)

Guidance literature:

(2S)-amino(cyclohexyl)ethanoic acid; With sodium carbonate; In water; Inert atmosphere;

(fluorenylmethoxy)carbonyl chloride; In 1,4-dioxane; water; for 8h; Inert atmosphere;

DOI:10.1021/jacs.5b12557

upstream raw materials:

(fluorenylmethoxy)carbonyl chloride

(2S)-amino(cyclohexyl)ethanoic acid

N-(9H-fluoren-2-ylmethoxycarbonyloxy)succinimide

Refernces

• 1、 -. "EPHA4 CYCLIC PEPTIDE ANTAGONISTS AND METHODS OF USE THEREOF". Paragraph 0632-0633; 0639; 0775-0777. . Retrieved 2019/11/19.