(S)-2-((((9H-Fluoren-9-yl)methoxy)carbonyl)(methyl)amino)-3-cyclohexylpropanoic acid

Base Information

• Chemical Name: (S)-2-((((9H-Fluoren-9-yl)methoxy)carbonyl)(methyl)amino)-3-cyclohexylpropanoic acid
• CAS No.: 148983-03-3
• Molecular Formula: C25H29NO4
• Molecular Weight: 407.51
• Mol file: 148983-03-3.mol

Synonyms:(S)-2-((((9H-Fluoren-9-yl)methoxy)carbonyl)(methyl)amino)-3-cyclohexylpropanoic acid;(S)-2-((((9H-Fluoren-9-yl)methoxy)carbonyl)(m...

Chemical Property of (S)-2-((((9H-Fluoren-9-yl)methoxy)carbonyl)(methyl)amino)-3-cyclohexylpropanoic acid

Chemical Property:

• Boiling Point: 588.5±29.0 °C(Predicted)
• PKA: 3.92±0.10(Predicted)
• PSA: 66.84000
• Density: 1.198±0.06 g/cm3(Predicted)
• LogP: 5.29090
• Storage Temp.: 2-8°C

Purity/Quality:

99%+, ^*data from raw suppliers

(S)-2-((((9H-Fluoren-9-yl)methoxy)carbonyl)(methyl)amino)-3-cyclohexylpropanoicacid 97% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of (S)-2-((((9H-Fluoren-9-yl)methoxy)carbonyl)(methyl)amino)-3-cyclohexylpropanoic acid

There total 2 articles about (S)-2-((((9H-Fluoren-9-yl)methoxy)carbonyl)(methyl)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: 84.0%

(4S)-3<<(9-fluorenylmethyl)oxy>carbonyl>-4-(cyclohexyl)methyl-5-oxooxazolidine → (S)-2-({[(9H-fluoren-9-yl)methoxy]carbonyl}(methyl)amino)-3-cyclohexylpropanoic acid (148983-03-3,1210834-55-1)

Guidance literature:

With triethylsilane; aluminum (III) chloride; In dichloromethane; at 20 ℃; for 16h;

DOI:10.1021/acsmedchemlett.0c00154

Reference yield:

(S)-3-cyclohexyl-2-(9H-fluoren-9-ylmethoxycarbonylamino)propionic acid (135673-97-1) → (S)-2-({[(9H-fluoren-9-yl)methoxy]carbonyl}(methyl)amino)-3-cyclohexylpropanoic acid (148983-03-3,1210834-55-1)

Guidance literature:

Multi-step reaction with 2 steps

1: 78 percent / TsOH*H₂O / toluene / 1 h / Heating

2: 53 percent / Et₃SiH / CHCl₃ / 5 h / Ambient temperature

With triethylsilane; toluene-4-sulfonic acid; In chloroform; toluene;

DOI:10.1021/jm00047a020

Reference yield: 89.0%

benzyl bromide (100-39-0) + (S)-2-({[(9H-fluoren-9-yl)methoxy]carbonyl}(methyl)amino)-3-cyclohexylpropanoic acid (148983-03-3,1210834-55-1) → Fmoc-N-Me-Cha-OBn

Guidance literature:

(S)-2-({[(9H-fluoren-9-yl)methoxy]carbonyl}(methyl)amino)-3-cyclohexylpropanoic acid; With potassium carbonate; In N,N-dimethyl-formamide; at 0 ℃; for 1h;

benzyl bromide; In N,N-dimethyl-formamide; at 0 - 20 ℃;

DOI:10.1039/d1md00120e

upstream raw materials:

(S)-3-cyclohexyl-2-(9H-fluoren-9-ylmethoxycarbonylamino)propionic acid

Downstream raw materials:

((S)-1-tert-Butylcarbamoyl-2-cyclohexyl-ethyl)-methyl-carbamic acid 9H-fluoren-9-ylmethyl ester

(2S)-α-(methylamino)-N-(1,1-dimethylethyl)cyclohexanepropionamide

Refernces

• 1、 Gmeiner, Peter,Hübner, Harald,Kaindl, Jonas,Kl?sel, Ilona,Schmidt, Maximilian F.,Weikert, Dorothee. "Discovery of Novel Nonpeptidic PAR2 Ligands". supporting information. p. 1316 - 1323. Retrieved 2020/07/04.