13490-76-1

Upstream product

• 769-68-6 2-phenylbutanenitrile 
• 90-26-6 2-phenylbutyramide 
• 90-27-7 2-Phenylbutyric acid 
• 40473-35-6 (S)-(+)-2-phenylbutyric acid chloride 
• 4286-15-1 (S)-2-phenylbutyric acid 

Downstream Products

• 90-27-7 2-Phenylbutyric acid 
• 33603-06-4 (+)-1-amino-2-phenylbutane 
• 56652-56-3 (S)-2-phenyl-butyronitrile 
• 1337959-54-2 C₁₁H₁₁NOS₂ 
• 1337959-56-4 C₁₁H₁₁NOS₂ 

Relevant academic research and scientific papers

Absolute configuration and polymorphism of 2-phenylbutyramide and α-methyl-α-phenylsuccinimide

Crystal structures of racemic and homochiral forms of 2-phenylbutyramide (1) and 3-methyl-3-phenylpyrrolidine-2,5-dione (2) were investigated in detail by a single crystal X-ray diffraction study. Absolute configurations of the homochiral forms of 1 and 2, obtained by chromatographic separation of racemates, were determined. It was revealed that racemate and homochiral forms of 1 are very similar in terms of supramolecular organization (H-bonded ribbons) in crystal, infrared (IR) spectral characteristics, and melting points. The presence of two different molecular conformations in homochiral forms of 1 allowed mimicking of crystal packing of the H-bonded ribbons in racemate 1. Two polymorph modifications (monoclinic and orthorhombic) comprising very similar H-bonded zigzag-like chains were found for the homochiral forms of compound 2 that were significantly different in terms of crystal structure, IR spectra, and melting points from the racemic form of 2. Unlike compound 1, homochiral forms of compound 2 have a higher density than the corresponding racemate which contradicts the Wallach rule and indicates that, in this case, homochiral forms are more stable than racemate forms.

Synthesis of chiral disulfides: Potential reagents for enantioselective sulfurization

Synthesis of chiral phosphorothioates for use as antisense oligonucleotides might benefit from the use of chiral disulfides. This paper reports the synthesis of chiral analogs of phenylacetyl disulfide and of 5-methyl-3H-1,2,4-dithiazol-3-one from the same set of 2-arylalkanoic acids. The X-ray crystal structures of the disulfides derived from (R) and [S]-2-phenylpropanoic acid establish the stereochemistry and the helicity of these materials, and density functional theory calculations suggest that the high specific rotations can be due to preferred retention of this helicity in solution. Chiral HPLC showed that the final products were formed with enantiomeric purities from 86.1% to >99.9%.

Probing the enantioselectivity of a diverse group of purified cobalt-centred nitrile hydratases

In this study a diverse range of purified cobalt containing nitrile hydratases (NHases, EC 4.2.1.84) from Rhodopseudomonas palustris HaA2 (HaA2), Rhodopseudomonas palustris CGA009 (009), Sinorhizobium meliloti 1021 (1021), and Nitriliruptor alkaliphilus (iso2), were screened for the first time for their enantioselectivity towards a broad range of chiral nitriles. Enantiomeric ratios of >100 were found for the NHases from HaA2 and CGA009 on 2-phenylpropionitrile. In contrast, the Fe-containing NHase from the well-characterized Rhodococcus erythropolis AJ270 (AJ270) was practically aselective with a range of different α-phenylacetonitriles. In general, at least one bulky group in close proximity to the α-position of the chiral nitriles seemed to be necessary for enantioselectivity with all NHases tested. Nitrile groups attached to a quaternary carbon atom were only reluctantly accepted and showed no selectivity. Enantiomeric ratios of 80 and >100 for AJ270 and iso2, respectively, were found for the pharmaceutical intermediate naproxennitrile, and 3-(1-cyanoethyl)benzoic acid was hydrated to the corresponding amide by iso2 with an enantiomeric ratio of >100.

BICYCLIC LACTAM FACTOR VIIA INHIBITORS USEFUL AS ANTICOAGULANTS

The present invention provides novel bicyclic lactams derivatives, and analogues thereof, of Formula (I): or a stereoisomer, tautomer, pharmaceutically acceptable salt, solvate, or prodrug thereof, wherein the variables A, B, C, W, Y, Z1, Z2, Z3, Z4, R8, and R9 are as defined herein. These compounds are selective inhibitors of factor VIIa which can be used as medicaments.

Stereoselective Hydrolysis of Nitriles and Amides Under Mild Conditions Using a Whole Cell Catalyst

An immobilised whole cell Rhodococcus sp. (SP 361) has been shown to be an effective catalyst for the stereoselective hydrolysis of both racemic and prochiral nitrile containing compounds. 2-Alkyl-arylacetonitriles 6a-8a were hydrolysed to (S)-acids and (R)-amides whereas the closely related substrate 9a gave the (R)-acid.A series of prochiral dinitriles 10a-13a were hydrolysed to the corresponding (S)-acids with e.e.'s 22-84percent.Models to account for the stereoselectivity of the enzymic hydrolyses have been proposed.

Enantioselective hydrolysis of nitriles and amides using an immobilised whole cell system

An immobilised whole cell catalyst SP361 has been shown to hydrolyse a range of 2-alkyl arylacetonitriles 1a-3a and amides 2b, 3b with good to excellent enantioselectivity. The absolute configuration of the derived amides and/or carboxylic acids shows remarkable changes according to the structure of the nitrile substrate.