(3R)-3-azaniumyl-3-(4-chlorophenyl)propanoate

Base Information

• Chemical Name: (3R)-3-azaniumyl-3-(4-chlorophenyl)propanoate
• CAS No.: 131690-61-4
• Molecular Formula: C₉H₁₀ClNO₂
• Molecular Weight: 199.637
• Hs Code.: 2922498590
• Mol file: 131690-61-4.mol

Synonyms:AKOS015890582

Chemical Property of (3R)-3-azaniumyl-3-(4-chlorophenyl)propanoate

Chemical Property:

• Vapor Pressure: 3.54E-05mmHg at 25°C
• Melting Point: 241-244 °C (sublm)(Solv: water (7732-18-5); acetone (67-64-1))
• Refractive Index: 1.589
• Boiling Point: 345.8 °C at 760 mmHg
• PKA: 3.62±0.10(Predicted)
• Flash Point: 162.9 °C
• PSA: 63.32000
• Density: 1.333 g/cm³
• LogP: 2.51480
• Storage Temp.: Keep in dark place,Inert atmosphere,Room temperature
• XLogP3: -0.1
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 2
• Exact Mass: 199.0400063
• Heavy Atom Count: 13
• Complexity: 173

Purity/Quality:

99% ^*data from raw suppliers

(R)-3-Amino-3-(4-chloro-phenyl)-propionicAcid ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC(=CC=C1C(CC(=O)[O-])[NH3+])Cl
• Isomeric SMILES: C1=CC(=CC=C1[C@@H](CC(=O)[O-])[NH3+])Cl
• Uses: (R)-3-Amino-3-(4-chloro-phenyl)-propionic Acid is used in the synthesis of N-Benzoyl Phenylisoserinoyl side-chain of the anticancer drug taxol.

Technology Process of (3R)-3-azaniumyl-3-(4-chlorophenyl)propanoate

There total 34 articles about (3R)-3-azaniumyl-3-(4-chlorophenyl)propanoate 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: 86.0%

p-chlorocinnamic acid (1615-02-7,940-62-5) → p-chlorophenylalanine (14173-39-8,1991-78-2) + (R)-β-amino-β-(4-chlorophenyl)propionic acid (131690-61-4)

Guidance literature:

With ammonia; at 25 ℃; pH=9; regioselective reaction; Kinetics; aq. buffer; Enzymatic reaction;

DOI:10.1002/anie.201106372

Reference yield: 70.0%

β-(N-phenylacetylamino)-β-(4-chlorophenyl)propionic acid (171002-19-0) → (R)-β-amino-β-(4-chlorophenyl)propionic acid (131690-61-4)

Guidance literature:

With potassium hydroxide; Ambient temperature; penicillin acylase (EC 3.5.1.11), pH 7.5;

DOI:10.1016/0957-4166(95)00204-3

Reference yield: 65.0%

3-(4-Chloro-phenyl)-3-hydroxyamino-propionic acid (197785-39-0) → 3-amino-3-(4-chlorophenyl)propionic acid (19947-39-8,131690-61-4)

Guidance literature:

With sodium hydroxide; zinc; at 20 ℃; for 6h;

DOI:10.1071/C96216

upstream raw materials:

malonic acid

4-chlorobenzaldehyde

3-(4-Chloro-phenyl)-3-hydroxyamino-propionic acid

3-(4-chlorophenyl)prop-2-enoic acid

Downstream raw materials:

methyl (S)-3-amino-3-(4-chlorophenyl)propanoate

(S)-β-amino-β-(4-chlorophenyl)propionic acid

Refernces

• 1、 Baba, Souya,Hirano, Kazuki,Tayama, Eiji. "Base-induced Sommelet–Hauser rearrangement of N-(α-(2-oxyethyl)branched)benzylic glycine ester-derived ammonium salts via a chelated intermediate". supporting information. . Retrieved 2020/03/13.
• 2、 Zhou, Wei,Xiao, Qingwei,Chang, Yuanyuan,Liu, Qifa,Zang, Xiaohao,Hu, Mengmeng,Zeng, Xi,Du, Zhiyun,Zhong, Guifa. "Substrate-controlled Diastereoselective Michael Addition of Alkylidene Malonates by Grignard Reagents". . p. 116 - 121. Retrieved 2019/12/14.