77184-10-2

Upstream product

• 34619-03-9 tert-butyldicarbonate 
• 66324-10-5 tert-butyldimethyl(1-phenylvinyloxy)silane 
• 140170-90-7 tert-butyl N-[2-[methoxy(methyl)amino]-2-oxo-ethyl]-N-methyl-carbamate 
• 100-58-3 phenylmagnesium bromide 
• 124072-76-0 tert-butyl methyl(2-morpholino-2-oxoethyl)carbamate 
• 13734-36-6 N-(tert-butoxycarbonyl)sarcosine 
• 24424-99-5 di-tert-butyl dicarbonate 
• 76467-34-0 hydrobromide salts of N-methylphenacylamine 
• 70-11-1 α-bromoacetophenone 
• 5468-37-1 2-aminoacetophenone hydrochloride 
• 73286-37-0 N-(2-oxo-2-phenylethyl)formamide 
• 68579-60-2 2-(methylamino)-1-phenylethanol 
• 7541-17-5 tert-butyl N,N-dimethylcarbamate 
• 98-88-4 benzoyl chloride 

Downstream Products

• 76467-28-2 N-Methyl-N-phenacylformamid 
• 291533-26-1 (R)-2-[(tert-butoxycarbonyl)(methyl)amino]-1-phenylethanol 
• 23826-47-3 2-(methylamino)-1-phenylethanone hydrochloride 
• 77184-12-4 rac-3-hydroxy-1-methyl-3-phenylazetidin-2-one 
• 495-42-1 (-)-Halostachine 

Relevant academic research and scientific papers

Visible-Light-Mediated Amination of π-Nucleophiles with N-Aminopyridinium Salts

N-Aminopyridinium salts generate nitrogen-centered radicals by means of photoredox catalysis. Herein, we report that they can be trapped by enol equivalents to give α-amino carbonyl compounds in excellent yields. The broad synthetic utility of this method is demonstrated by functionalization of ketones, aldehydes, esters enol equivalents, vinyl ethers, and 1,3-diketones without the need for prior conversion to enol derivatives. The developed method is easily scalable, offers broad substrate scope, high chemoselectivity.

COMPOSITIONS AND METHODS COMPRISING SUBSTITUTED 2-AMINOIMIDAZOLES

The present invention presents 2-(acylamino)imidazoles with therapeutic activity, including selective activity against cancer cells, and compositions comprising them. Methods of using and preparing the 2-(acylamino)imidazoles are also presented.

COMPOUNDS USEFUL AS MODULATORS OF TRPM8

The present invention includes compounds useful as modulators of TRPM8, such as compounds of Formulae (Ia), (Ib) and (Ic), and the subgenus and species thereof; personal products containing those compounds; and the use of those compounds and the personal products, particularly the use of increasing or inducing chemesthetic sensations, such as cooling or cold sensations.

Investigation of the mechanism of racemization of litronesib in aqueous solution: Unexpected base-catalyzed inversion of a fully substituted carbon chiral center

Mitosis inhibitor (R)-litronesib (LY2523355) is a 1,3,4-thiadiazoline- bearing phenyl and N-(2-ethylamino)ethanesulfonamido-methyl substituents on tetrahedral C5. Chiral instability has been observed at pH 6 and above with the rate of racemization increas

Ligand-controlled α- And β-arylation of acyclic N-boc amines

The palladium-catalyzed ligand-controlled arylation of α-zincated acyclic amines, obtained by directed α-lithiation and transmetalation, is described. Whereas PtBu3 gave rise to α-arylated Boc-protected amines, more flexible N-phenylazole-based phosphine ligands induced major β-arylation through migrative cross-coupling. All manner of control: The arylation of α-zincated acyclic Boc-protected amines was selectively performed at the α- or β-position in a ligand-controlled manner. α-Arylation occurs by direct reductive elimination of the α-palladated intermediate whereas β-arylation involves palladium migration along the alkyl chain. Boc=tert-butoxycarbonyl.

Practical enzymatic desymmetrization of 2-(ethoxycarbonyl)propane-1,3-diyl dihexanoate and model cyclization for the A-D ring system of lysergic acid

Porcine pancreas lipase-catalyzed hydrolysis of symmetrical 2-(ethoxycarbonyl)propane-1,3-diyl dihexanoate, under the modified conditions of the Seebach protocol, afforded a desymmetrized monohexanoate in 40-51% yield with 91-94% ee, even in a gram-scale reaction. The absolute configuration of a half-hydrolyzed (-)-product was determined to be (R) by conversion to a known 2-methylpropane-1,3-diol derivative. Samarium iodide-induced radical cyclization of 2-oxo-3-phenylethylamine with a C4 unit on the N-atom, derived from the racemic monohexanoate, afforded a 3-phenylpiperidine derivative as a model construction of the A-D ring system of lysergic acid.

Acylation of α-(N-carbamoyl)alkylcuprates and alkyl- or aryl(halo)cuprates

α-(N-Carbamoyl)alkylcuprates [R2CuLi·LiX or RCuXLi (X=CN, Cl)] when prepared from THF soluble CuX·2LiCl (X=Cl, CN) undergo a reliable and generally high yield reaction with aroyl, alkanoyl, and alkenoyl chlorides to provide a rapid and efficient synthesis of α-carbamoyl ketones. Cuprates prepared from acyclic, cyclic, and a functionalized carbamate can be utilized. Although yields are a function of cuprate reagent and substrate structure, nearly quantitative yields can be obtained with reagents generated from 2RLi+CuCN·2LiCl. The use of reagents generated from CuCl·2LiCl are more efficient in the α-(N-carbamoyl)alkyl ligand, although yields are slightly lower. Acylation of alkyl(chloro)cuprates generated from one equivalent of CuCl·2LiCl and organolithium or Grignard reagents provides an efficient and high yield procedure for ketone synthesis.

Acylation of α-aminoalkyl- copper and cuprate reagents with acid chlorides: Improved yields with soluble copper (I) salts

α-Aminoalkylcopper reagents prepared from soluble CuX·2LiCI give modest to good yields of α-aminoketones upon reaction with acid chlorides, Higher yields are generally obtained with CuCl·2LiCl than with CuCN·2LiCl. Improved yields can be obtained by utilization of cuprate reagents prepared from CuCN·2LiCl and 2.0 equivalents of α-lithiocarbamates.