500871-60-3

Usage

InChI:InChI=1/C11H22N2O3/c1-6-13(7-2)9(14)8-12-10(15)16-11(3,4)5/h6-8H2,1-5H3,(H,12,15)

Upstream product

• 3392-07-2 tert-butyl N-{2-[(2,5-dioxopyrrolidin-1-yl)oxy]-2-oxoethyl}carbamate 
• 109-89-7 diethylamine 
• 133010-01-2 1,1-dimethylethyl N-(fluorocarbonylmethyl)carbamate 
• 4530-20-5 BOC-glycine 
• 36016-38-3 tert-Butyl N-hydroxycarbamate 
• 40052-13-9 mono-tert-butyl malonate 

Downstream Products

• 108723-79-1 N,N-diethyl-2-aminoacetamide hydrochloride 
• 877880-03-0 N,N-diethyl-2-(methylamino)acetamide hydrochloride 
• 934548-15-9 [2-(2,6-dichloro-phenylamino)-phenyl]-acetic acid diethylcarbamoylmethylcarbamoyloxymethyl ester 

Relevant academic research and scientific papers

Carboxylic Acid Deoxyfluorination and One-Pot Amide Bond Formation Using Pentafluoropyridine (PFP)

This work describes the application of pentafluoropyridine (PFP), a cheap commercially available reagent, in the deoxyfluorination of carboxylic acids to acyl fluorides. The acyl fluorides can be formed from a range of acids under mild conditions. We also demonstrate that PFP can be utilized in a one-pot amide bond formation via in situ generation of acyl fluorides. This one-pot deoxyfluorination amide bond-forming reaction gives ready access to amides in yields of ≤94%.

Synthesis of protected α-amino acids: Via decarboxylation amination from malonate derivatives

A general and efficient strategy for the synthesis of protected α-amino acids is reported. The method uses malonate derivatives as the starting materials and Cs2CO3 as a base at 60 degrees, giving α-amino acid derivatives in moderate yields by releasing CO2. This methodology shows broad substrate scope (primary and secondary acids), excellent functional group tolerance and high efficiency to give the desired products under mild reaction conditions. It also allows the construction of β and γ-amino acids and other unnatural products.

ADENOSINE RECEPTOR BINDING COMPOUNDS

The present invention relates to pharmaceutical compounds and compositions of Formula (I) and methods of treatment using the compounds and compositions, especially for the treatment and/or prevention of a proliferation disorder, such as cancer. Compounds of Formula (I) as further described herein are shown modulators of the adenosine A2A receptor and exhibit antiproliferative activity. Accordingly, these compounds are useful to treat proliferative disorders such as cancer, and other adenosine receptor-related conditions including an inflammatory disease, renal disease, diabetes, vascular disease, lung disease, or an autoimmune disease.

Glycinamide hydrochloride as a transient directing group: Synthesis of 2-benzylbenzaldehydes by C(sp3)?H arylation

Glycinamide hydrochloride as an inexpensive and commercially available transient directing group for the C(sp3)?H arylation of 2-methylbenzaldehydes is described. A series of practical 2-benzylbenzaldehydes bearing various functional groups are efficiently synthesized in satisfactory yield by this strategy. This method can also be extended to gram scale.

Base catalytic decarboxylation amination preparation method of amino-acid ester/amide

The invention discloses a base catalytic preparation method of alpha amino-acid ester/amide from beta carbonyl acid, and belongs to the field of organic chemistry. According to the method, malonate is taken as a raw material, single hydrolysis is carried out to obtain beta carbonyl acid, reaction with a hydroxylamine compound is carried out to obtain an acyloxyl carbamic acid ester, and under the effect of an alkali, removing of one molecule carbon dioxide is carried out so as to obtain an alpha amino-acid ester, wherein the process of synthesis of the alpha amino-acid ester/amide is similar to the above process. The raw materials are widely available; operation is simple and convenient; reaction conditions are mild; using of toxic cyanide and derivatives of cyanide, strong oxidizing/reducing agents, and precious metal catalysts in a conventional alpha amino acid synthesis method is avoided; and requirements of the trend of green chemistry development are satisfied.

Aminocarbonyloxymethyl ester prodrugs of flufenamic acid and diclofenac: Suppressing the rearrangement pathway in aqueous media

Aminocarbonyloxymethyl ester prodrugs are known to undergo rearrangement in aqueous solutions to form the corresponding N-acylamine side product via an O → N intramolecular acyl transfer from the carbamate conjugate base. Novel aminocarbonyloxymethyl esters of diclofenac and flufenamic acid containing amino acid amide carriers were synthesized and evaluated as potential prodrugs displaying less ability to undergo rearrangement. These compounds were prepared in reasonable yield by a four-step synthetic method that uses the appropriate N-Boc-protected amino acid N-hydroxysuccinimide ester and secondary amine and chloromethyl chloroformate as key reactants. Their reactivity in pH 7.4 buffer and 80% human plasma at 37°C was assessed by RP-HPLC. The aminocarbonyloxymethyl esters containing a secondary carbamate group derived from amino acids such as glycine or phenylalanine were hydrolyzed quantitatively to the parent drug both in non-enzymatic and enzymatic conditions, with no rearrangement product being detected. The oral bioavailability in rats was determined for selected diclofenac derivatives. These derivatives displayed a bioavailability of 25 to 68% relative to that of diclofenac, probably due to their poor aqueous solubility and lipophilicity. These results suggest that further optimization of aminocarbonyloxymethyl esters as potential prodrugs for non-steroidal anti-inflammatory drugs require the use of amino acid carriers with ionizable groups to improve aqueous solubility.