(3S)-4-cyano-3-phenylbutanoic acid

Base Information

• Chemical Name: (3S)-4-cyano-3-phenylbutanoic acid
• CAS No.: 321125-69-3
• Molecular Formula: C₁₁H₁₁NO₂
• Molecular Weight: 189.214
• Mol file: 321125-69-3.mol

Synonyms:(3S)-4-cyano-3-phenylbutanoic acid

Chemical Property of (3S)-4-cyano-3-phenylbutanoic acid

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3S)-4-cyano-3-phenylbutanoic acid

There total 4 articles about (3S)-4-cyano-3-phenylbutanoic 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:

3-phenylglutaronitrile (78533-73-0) → (3S)-4-cyano-3-phenylbutanoic acid (321125-69-3)

Guidance literature:

With Herbaspirillum sp. GW₁₀₃ nitrilase; In aq. phosphate buffer; at 30 ℃; for 16h; pH=7.5; enantioselective reaction; Enzymatic reaction;

DOI:10.1007/s11426-014-5139-2

Reference yield:

3-phenylglutaronitrile (78533-73-0) → (3R)-4-cyano-3-phenylbutanoic acid + (3S)-4-cyano-3-phenylbutanoic acid (321125-69-3)

Guidance literature:

With phosphate buffer; Rhodococcus sp. AJ₂₇₀; In acetone; at 30 ℃; for 24h; pH=7; Title compound not separated from byproducts; Enzymatic reaction;

DOI:10.1016/S0040-4039(00)01518-5

Reference yield:

dimethyl 2-(2-cyano-1-phenylethyl)malonate → (3S)-4-cyano-3-phenylbutanoic acid (321125-69-3)

Guidance literature:

Multi-step reaction with 2 steps

1: potassium hydroxide / water; ethanol / 16 h / 20 °C

2: m-xylene / 5 h / Inert atmosphere; Reflux

With potassium hydroxide; In ethanol; water; m-xylene;

DOI:10.1039/c5cc05158d

upstream raw materials:

3-phenylglutaronitrile

Downstream raw materials:

(S)-Phenibut

(R)-Phenibut

((R)-3-Cyano-2-phenyl-propyl)-carbamic acid methyl ester

Refernces

• 1、 Wang,Liu,Li,Meth-Cohn. "Microbial desymmetrization of 3-arylglutaronitriles, an unusual enhancement of enantioselectivity in the presence of additives". . p. 8549 - 8552. Retrieved 2000.
• 2、 Aitken, Lewis S.,Hammond, Lisa E.,Sundaram, Rajkumar,Shankland, Kenneth,Brown, Geoffrey D.,Cobb, Alexander J.A.. "Asymmetric cyclopropanation of conjugated cyanosulfones using a novel cupreine organocatalyst: Rapid access to δ3-amino acids". . p. 13558 - 13561. Retrieved 2015/09/01.