77320-41-3

Upstream product

• 67-56-1 methanol 
• 37127-06-3 2-phenyl-4-acetyl-5-oxazolinone 
• 99972-61-9 2-phenyl-4-α-hydroxyethylidene-5-oxazolone 
• 1205-08-9 methyl hippurate 
• 75-36-5 acetyl chloride 
• 79893-89-3 N-benzoyl-L-threonine methyl ester 
• 68277-01-0 2-amino-3-oxo-butyric acid methyl ester 
• 98-88-4 benzoyl chloride 
• 124576-57-4 C₁₀H₁₇NO₅ 
• 495-69-2 Hippuric Acid 
• 87413-09-0 Dess-Martin periodane 
• 41172-77-4 (±)-2-amino-3-oxo-butyric acid methyl ester hydrochloride 
• 24762-04-7 2-Diazo-3-oxo-butyric acid methyl ester 
• 55-21-0 benzamide 

Downstream Products

• 79893-89-3 N-benzoyl-L-threonine methyl ester 
• 60538-16-1 (2R,3S)-N-benzoylthreonine methyl ester 
• 18735-74-5 5-methyl-2-phenyloxazole-4-carboxylic acid 
• 591741-72-9 methyl 5-methyl-1,2-diphenyl-1H-imidazole-4-carboxylate 

Relevant academic research and scientific papers

Transformation of 4-(1-dimethylaminoethylidene)-2-phenyl-5(4H) oxazolone into methyl 2-benzoylamino-3-oxobutanoate. The synthesis of 1-substituted 4- benzoylamino-3-methyl-5(2H)-pyra-zolones

Methyl 2-benzoylamino-3-oxobutanoate (3) was prepared from hippuric acid (1) which was converted with N,N-dimethylacetamide and phosphorus oxychloride into 4-(1-dimethylaminoethylidene)-2-phenyl-5(4H)-oxazolone (2) followed by hydrolysis with hydrochloric acid in methanol. Compound 3 was treated with hydrazines 4 to give 4-benzoylamino-3-methyl-1H-pyrazol-5(2H)-one (6a) and its 1-substituted derivatives 6b-j. The corresponding hydrazones 5f, i, j were isolated as intermediates.

Rhodium carbene routes to oxazoles and thiazoles. Catalyst effects in the synthesis of oxazole and thiazole carboxylates, phosphonates, and sulfones

(Chemical Equation Presented) Dirhodium tetraacetate catalyzed reaction of α-diazo-β-keto-carboxylates and -phosphonates with arenecarboxamides gives 2-aryloxazole-4-carboxylates and 4-phosphonates by carbene N-H insertion and cyclodehydration. In stark contrast, dirhodium tetrakis(heptafluorobutyramide) catalysis results in a dramatic change of regioselectivity to give oxazole-5-carboxylates and 5-phosphonates. α-Diazo-β-ketosulfones behave similarly and give 5-sulfonyloxazoles upon dirhodium tetrakis-(heptafluorobutyramide) catalyzed reaction with carboxamides. The analogous reactions of thiocarboxamides give the corresponding thiazole-5-carboxylates, -phosphonates, and -sulfones. 2009 American Chemical Society.

The rhodium carbene route to oxazoles: A remarkable catalyst effect

Dirhodium tetraacetate catalysed reaction of α-diazo-β-keto- carboxylates and -phosphonates with arenecarboxamides gives 2-aryloxazole-4- carboxylates and 4-phosphonates by carbene N-H insertion and cyclodehydration; in stark contrast, dirhodium tetrakis(

Towards Gram-negative antivirulence drugs: New inhibitors of HldE kinase

Gram-negative bacteria lacking heptoses in their lipopolysaccharide (LPS) display attenuated virulence and increased sensitivity to human serum and to some antibiotics. Thus inhibition of bacterial heptose synthesis represents an attractive target for the development of new antibacterial agents. HldE is a bifunctional enzyme involved in the synthesis of bacterial heptoses. Development of a biochemical assay suitable for high-throughput screening allowed the discovery of inhibitors 1 and 2 of HldE kinase. Study of the structure-activity relationship of this series of inhibitors led to highly potent compounds.

Pd-catalyzed enantioselective synthesis of quaternary α-amino acid derivatives using a phenylalanine-derived P-chirogenic diaminophosphine oxide

A Pd-catalyzed enantioselective synthesis of quaternary α-amino acid derivatives using a phenylalanine-derived P-chirogenic diaminophosphine oxide is described. Asymmetric allylic substitution using acyclic β-keto esters with a nitrogen functional group at the α-carbon as prochiral nucleophiles proceeded in the presence of 5 mol % of Pd catalyst, 10 mol % of chiral diaminophosphine oxide 1j, BSA, and appropriate additives, affording the corresponding quaternary α-amino acid derivatives in excellent yield and in up to 92% ee.

Combinatorial synthesis and biological evaluation of library of small-molecule Ser/Thr-protein phosphatase inhibitors

In eukaryotes, phosphorylation of serine, threonine, and tyrosine residues on proteins is a fundamental posttranslational regulatory process for such functions as signal transduction, gene transcription, RNA splicing, cellular adhesion, apoptosis, and cell cycle control. Based on functional groups present in natural product serine/threonine protein phosphatase (PSTPase) inhibitors, we have designed pharmacophore model 1 and demonstrated the feasibility of a combinatorial chemistry approach for the preparation of functional analogues of 1. Preliminary biological testing of 18 structural variants of 1 has identified two compounds with growth inhibitory activity against cultured human breast cancer cells. In vitro inhibition of the PSTPase PP2A was demonstrated with compound Id. Using flow cytometry we observed that compound If caused prominent inhibition in the G1 phase of the cell cycle. Thus, the combinatorial modifications of the minimal pharmacophore 1 can generate biologically interesting antiproliferative agents.

Thiazolidinedione derivatives as hypoglycemic agents

Hypoglycemic thiazolidine-2,4-dione derivatives of the formula STR1 wherein the dotted line represents a bond or no bond; V is --CH=CH--, --N=CH--, --CH=N--, S, O or NR; W is S, SO, SO2, SO2 NR1, NR1 SO2/s

Thiazolidinedione derivatives as hypoglycemic agents

Hypoglycemic thiazolidine-2,4-dione derivatives of the formula wherein the dotted line represents a bond or no bond;, V is -CH=CH-, -N=CH-, -CH=N-, S, O or NR;, W is S, SO, SO2, SO2NR1, NR1SO2, CONR1 or NR1CO;, X is S, O,