60131-32-0

Upstream product

• 74626-57-6 2-(3-(2-phenyl-1,3-dioxolan-2-yl)phenyl)propanal 

Downstream Products

• 1173289-23-0 (2S)-[3-(2-hydroxy-1-methyl-ethyl)-phenyl]-phenyl-methanone 
• 114937-08-5 (4R)-2-[1-(3-benzoylphenyl)-ethyl]-thiazolidine-4-carboxylic acid hydrochloride 

Relevant academic research and scientific papers

Chemoenzymatic synthesis of (2S)-2-arylpropanols through a dynamic kinetic resolution of 2-arylpropanals with alcohol dehydrogenases

We applied Horse Liver Alcohol Dehydrogenase (HLADH) to the enantioselective synthesis of six (2S)-2-arylpropanols, useful intermediates in the synthesis of Profens. The influence of substrate structure and reaction conditions on yields and enantioselectivity were investigated. The high yields and high enantioselectivity towards the (S)-enantiomer obtained in the bioreduction of 2-arylpropionic aldehydes, clearly indicate the achievement of a DKR process through a combination of an enzyme-catalyzed kinetic reduction with a chemical base-catalyzed racemization of the unreacted aldehydes. The racemization step is represented by the keto-enol equilibrium of the aldehyde and can be controlled by modulating pH and reaction conditions.

Use of a robust dehydrogenase from an archael hyperthermophile in asymmetric catalysis-dynamic reductive kinetic resolution entry into (s)-profens

Described is an efficient heterologous expression system for Sulfolobus solfataricus ADH-10 (Alcohol Dehydrogenase isozyme 10) and its use in the dynamic reductive kinetic resolution (DYRKR) of 2-arylpropanal (Profen-type) substrates. Importantly, among the 12 aldehydes tested, a general preference for the (S)-antipode was observed, with high ee's for substrates corresponding to the NSAIDs (nonsteroidal anti-inflammatory drugs) naproxen, ibuprofen, flurbiprofen, ketoprofen, and fenoprofen. To our knowledge, this is the first application of a dehydrogenase from this Sulfolobus hyperthermophile to asymmetric synthesis and the first example of a DYRKR with such an enzyme. The requisite aldehydes are generated by Buchwald-Hartwig-type Pd(0)-mediated α-arylation of tert-butyl propionate. This is followed by reduction to the aldehyde in one [lithium diisobutyl tert-butoxyaluminum hydride (LDBBA)] or two steps [LAH/Dess-Martin periodinane]. Treatment of the profenal substrates with SsADH in 5% EtOH/phosphate buffer, pH 9, with catalytic NADH at 80 °C leads to efficient DYRKR, with ee's exceeding 90% for 9 aryl side chains, including those of the aforementioned NSAIDs. An in silico model, consistent with the observed broad side chain tolerance, is presented. Importantly, the SsADH-10 enzyme could be conveniently recycled by exploiting the differential solubility of the organic substrate/product at 80 °C and at rt. Pleasingly, SsADH-10 could be taken through several thermal cycles, without erosion of ee, suggesting this as a generalizable approach to enzyme recycling for hyperthermophilic enzymes. Moreover, the robustness of this hyperthermophilic DH, in terms of both catalytic activity and stereochemical fidelity, speaks for greater examination of such archaeal enzymes in asymmetric synthesis.

Synthesis of aldehydes from carboxylic acids via N-methoxyimidoyl bromides: Deoximation of O-methyloximes

Aldehydes are synthesized by hydrogenation and subsequent deoximation of substituted N-methoxyalkanimidoyl bromides, which are prepared in one pot by reaction of the corresponding carboxylic acids with methoxyamine and triphenylphosphine carbon tetrabromide. Regeneration of aldehydes and ketones from O-methyloximes under mild conditions is also described.

Method for producing (aryl substituted) carboxylic acid or its salt

An effective method for producing highly pure (aryl substituted)carboxylic acid or its salt which comprises the steps of: (I) oxidizing (aryl substituted)aldehyde in an acidic phase in the presence of hypohalogenite; and (II) bringing the oxidized product obtained in the preceding step into contact in a liquid phase with hydrogen in the presence of a catalyst of transistion metal of the group VIII in the periodic table.

Pharmaceutically useful derivatives of thiazolidine-4-carboxylic acid

Compounds of formula in which R, R1 and Y have the meanings shown in the description, their preparation by condensing an aldehyde or a ketone with cysteine or a derivative thereof and their use in the pharmaceutical field. The compounds of formula I possess antipyretic, anti--inflammatory, mucolytic and analgesic activity together with a low capacity to cause gastric injuries. The compounds of formula I, furthermore, are particularly useful in the treatment of ischemia and reperfusion syndromes.