89232-29-1

Upstream product

• 882-36-0 N-benzyl-3-oxobutanamide 
• 3068-88-0 4-methyloxetan-2-one 
• 3287-99-8 benzylamine hydrochloride 
• 100-46-9 benzylamine 
• 300-85-6 3-Hydroxybutyric acid 

Downstream Products

• 127604-11-9 (R)-3,3,3-Trifluoro-2-methoxy-2-phenyl-propionic acid (R)-1-methyl-2-phenylcarbamoyl-ethyl ester 
• 127604-15-3 (R)-3,3,3-Trifluoro-2-methoxy-2-phenyl-propionic acid (R)-2-benzylcarbamoyl-1-methyl-ethyl ester 
• 127604-14-2 (R)-3,3,3-Trifluoro-2-methoxy-2-phenyl-propionic acid (S)-2-benzylcarbamoyl-1-methyl-ethyl ester 
• 127603-92-3 Methanesulfonic acid 2-benzylcarbamoyl-1-methyl-ethyl ester 
• 1018832-68-2 C₁₈H₁₉NO₃ 
• 146679-25-6 (R)-N-benzyl-3-hydroxybutyramide 
• 115395-12-5 (S)-N-benzyl-3-hydroxybutanamide 
• 51944-67-3 N-benzyl-3-methylpropenamide 
• 4391-83-7 1-benzyl-4-methylazetidinone 

Relevant academic research and scientific papers

Synthesis of α-Alkyl-β-Hydroxy Amides through Biocatalytic Dynamic Kinetic Resolution Employing Alcohol Dehydrogenases

Chiral (α-substituted) β-hydroxy amides are interesting derivatives as they are useful building blocks of many biologically active compounds. Herein, the biocatalytic stereocontrolled synthesis of various acyclic syn-α-alkyl-β-hydroxy amides through a dynamic kinetic resolution is shown. Hence, a series of overexpressed alcohol dehydrogenases (ADHs) in Escherichia coli was used to reduce the corresponding racemic β-keto amides. Among them, ADH-A from Rhodococcus ruber and commercial evo-1.1.200 afforded the best activities and selectivities, giving access to the opposite enantiomers with high diastereomeric excess and excellent enantiomeric excess. Some of these compounds were obtained at semipreparative scale. (Figure presented.).

B(OCH2CF3)3-mediated direct amidation of pharmaceutically relevant building blocks in cyclopentyl methyl ether

The use of B(OCH2CF3)3 for mediating direct amidation reactions of a wide range of pharmaceutically relevant carboxylic acids and amines is described, including numerous heterocycle-containing examples. An initial screen of solvents for the direct amidation reaction suggested that cyclopentyl methyl ether, a solvent with a very good safety profile suitable for use over a wide temperature range, was an excellent replacement for the previously used solvent acetonitrile. Under these conditions amides could be prepared from 18 of the 21 carboxylic acids and 18 of the 21 amines examined. Further optimisation of one of the low yielding amidation reactions (36% yield) via a design of experiments approach enabled an 84% yield of the amide to be obtained.

A mild method for ring-opening aminolysis of lactones

A mild and general method for lactone aminolysis is reported. Sodium 2-ethylhexanoate (NaEH) is found to serve both as a base and a catalyst in aminolysis of a variety of lactones by benzylamine hydrochloride. The nearly neutral pH conditions make this method applicable to many acid/base sensitive substrates.