69630-50-8

Basic information

• Product Name: D-ASPARTIC ACID DIMETHYL ESTER HYDROCHLORIDE
• Synonyms: H-D-ASP(OME)-OME HCL;H-D-ASP(ME)-OME HCL;D-ASPARTIC ACID-1,4-DIMETHYL ESTER HYDROCHLORIDE;D-ASPARTIC ACID DIMETHYL ESTER HCL;D-ASPARTIC ACID DIMETHYL ESTER HYDROCHLORIDE;D-ASPARTIC ACID ALPHA,BETA-DIMETHYL ESTER HYDROCHLORIDE;D-ASPARTIC ACID(OME)-OME HCL;DIMETHYL D-ASPARTATE HYDROCHLORIDE
• CAS NO: 69630-50-8
• Molecular Formula: C₆H₁₁NO₄*ClH
• Molecular Weight: 197.62
• EINECS: 1533716-785-6
• Product Categories: Amino Acids Derivatives;Amino ester;Amino hydrochloride
• Mol File: 69630-50-8.mol

Chemical Properties

• Melting Point: 114-119℃
• Appearance: /Solid
• Storage Temp.: −20°C
• Solubility: Methanol (Slightly), Water (Slightly)
• CAS DataBase Reference: D-ASPARTIC ACID DIMETHYL ESTER HYDROCHLORIDE(CAS DataBase Reference)
• NIST Chemistry Reference: D-ASPARTIC ACID DIMETHYL ESTER HYDROCHLORIDE(69630-50-8)
• EPA Substance Registry System: D-ASPARTIC ACID DIMETHYL ESTER HYDROCHLORIDE(69630-50-8)

Safety Data

• WGK Germany: 3
• Hazardous Substances Data: 69630-50-8(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
D-ASPARTIC ACID DIMETHYL ESTER HYDROCHLORIDE is used as a synthetic intermediate for the development of MK-7246 (M425045), a potent and selective CRTH2 antagonist. D-ASPARTIC ACID DIMETHYL ESTER HYDROCHLORIDE is being investigated for its potential therapeutic effects in the treatment of respiratory diseases, making it a valuable component in the pharmaceutical industry's efforts to create new and effective medications for respiratory conditions.

InChI:InChI=1/C6H11NO4.ClH/c1-10-5(8)3-4(7)6(9)11-2;/h4H,3,7H2,1-2H3;1H/t4-;/m1./s1

Upstream product

• 617-55-0 dimethyl (S)-malate 
• 67-56-1 methanol 
• 1783-96-6 (2R)-aspartic acid 
• 75-77-4 chloro-trimethyl-silane 

Downstream Products

• 151521-94-7 dimethyl (R)-N-(triphenylmethyl)aspartate 
• 155069-71-9 Dimethyl D-N-benzylaspartate 
• 151491-88-2 (R)-5-dimethoxyphosphoryl-4-oxo-N-(triphenylmethyl)norvaline methyl ester 
• 155069-72-0 Dimethyl D-N-(9-phenylfluoren-9-yl)-N-benzylaspartate 
• 155069-77-5 Dimethyl D-(3S)-N-(9-phenylfluoren-9-yl)-N-benzyl-3-methylaspartate 
• 130622-08-1 (2R)-2-tert-butoxycarbonylamino-succinic acid dimethyl ester 

Relevant articles and documents

2-(2-Hydroxyethyl)piperazine derivatives as potent human carbonic anhydrase inhibitors: Synthesis, enzyme inhibition, computational studies and antiglaucoma activity

Targeting Carbonic Anhydrases (CAs) represents a strategy to treat several diseases, from glaucoma to cancer. To widen the structure-activity relationships (SARs) of our series of piperazines endowed with potent human carbonic anhydrase (hCA) inhibition, a new series of chiral piperazines carrying a (2-hydroxyethyl) group was prepared. The Zn-binding function, the 4-sulfamoylbenzoyl moiety, was connected to one piperazine N-atom, while the other nitrogen was decorated with alkyl substituents. In analogy to the approach used for the synthesis of the previously reported series, the preparation of the new compounds started with (R)- and (S)-aspartic acid. A partial racemization occurred during the synthesis. In order to overcome this problem, other chemical strategies were investigated. The inhibitory activity of the new polar derivatives against four hCAs isoforms I, II, IV and IX using a stopped flow CO2 hydrase assay was determined. Some compounds showed potency in the nanomolar range and a preference for inhibiting hCA IX.

A Synthetic Route to the MT1-MMP Inhibitor Ancorinoside D

A methyl ester of ancorinoside D, a 3-acyltetramic acid metabolite of a sponge Penares sollasi, was synthesised in ten steps starting from a protected β- d -glucopyranosyl-(1→4)- d -galactopyranosyltrichloroacetimidate donor. Its attachment to the left half of the 3-acyl spacer by a Schmidt glycosylation, 2,2,6,6-tetramethylpiperidine-1-oxyl (TEMPO)-mediated oxidation to the uronic acid, introduction of the Z -alkene via Wittig reaction, and functionalisation of the spacer terminus with Meldrum's acid gave a β-keto ester that reacted with dimethyl N -methyl- d -aspartate under neutral conditions to afford a fully protected ancorinoside D as the product of an unusual domino N -acylation-Dieckmann condensation. Global deprotection left a methyl ester of ancorinoside D, which resisted all saponification attempts.

Preparation method of nitrogen-substituted aspartic acid

The invention discloses a preparation method of nitrogen-substituted aspartic acid, a nitrogen-substituted aspartic acid compound has the structural formula as shown in the specification, wherein R1 is alkyl, and R2 is an amino protecting group, and the preparation method can be used for preparation of the nitrogen-substituted aspartic acid from the nitrogen-substituted aspartic acid compound so as to reduce the cost of preparing the nitrogen-substituted aspartic acid and enables the nitrogen-substituted aspartic acid to be suitable for industrial production.

Preparation method of nitrogen-substituted aspartic acid

The invention discloses a preparation method of nitrogen-substituted aspartic acid, the method comprises the following steps: providing a nitrogen-substituted aspartic acid compound with the structural formula as shown in the specification, wherein R1 is alkyl, and R2 is an amino protecting group; performing deprotection treatment on the nitrogen-substituted aspartic acid compound to obtain the nitrogen-substituted aspartic acid with the structural formula as shown in the specification, and the preparation method disclosed by the invention can be used for reducing the cost of preparing the nitrogen-substituted aspartic acid and enabling the nitrogen-substituted aspartic acid to be suitable for industrial production.

Preparation method of sitagliptin intermediate

The invention discloses a preparation method of a sitagliptin intermediate and belongs to the field of medicine synthesis. The invention provides a preparation method of a compound 2; the compound 2 is prepared without the need of a catalyst and a resolving agent which have a high price and harsh low-temperature conditions, so that the cost is reduced to the great extent; the preparation method has the advantages of simple technology, high purity and high yield and is suitable for mass production.

A novel aggregation-induced emission enhancement triggered by the assembly of a chiral gelator: from non-emissive nanofibers to emissive micro-loops

In this study, a novel aggregation-induced emission (AIE) enhancement triggered by the self-assembly of chiral gelator is described. Tuning of molecular chirality in situ triggers different assemblies of superstructures exhibiting fluorescence. This novel AIE material can constitute an emerging library of chiral supramolecules for turn-on fluorescent sensors. It will also help in better understanding the effects of chiral factors on the photophysical process.

Pig growth urges the medicinal preparation preparation method of gene expression (by machine translation)

The invention discloses a Pig growth gene expression urges the medicinal preparation preparation method, the present invention relates to a synthesis of amino acid derivatives, in particular to a Pig growth gene expression urges the medicinal preparation D - aspartic acid derivatives, N - methyl - D - aspartic acid of preparation method, through D - aspartic acid as the raw material, the D - aspartic acid with methanol and thionyl chloride reaction generating D - aspartic acid dimethyl ester hydrochloride, then with 40% formaldehyde of the woven fabric under the alkaline condition generating N - hydroxymethyl - D - aspartic acid, using pd/c as the catalyst under normal temperature and pressure hydrogenation to obtain N - methyl - D - aspartic acid; simple preparation method of the invention, the prepared product quality is stable, and in the preparation of environmental pollution, can promote the growth of livestock and at the same time, improve the utilization rate of the feed and the improvement of the quality of the carcass raising the Pig, popularization and application. (by machine translation)

Rigidity versus Flexibility: Is This an Issue in σ1 Receptor Ligand Affinity and Activity?

Stereoisomeric 2,5-diazabicyclo[2.2.2]octanes 14 and 15 were prepared in a chiral-pool synthesis starting from (S)- or (R)-aspartate. The key step in the synthesis was a Dieckmann-analogous cyclization of (dioxopiperazinyl)acetates 8, which involved trapping of the intermediate hemiketal anion with Me3SiCl. The σ1 affinity was tested using membrane preparations from animal (Guinea pig) and human origin. The binding of bicyclic compounds was analyzed by molecular dynamics simulations based on a 3D homology model of the σ1 receptor. The good correlation between Ki values observed in the σ1 assays and calculated free binding energy, coupled with the identification of four crucial ligand/receptor interactions, allowed the formulation of structure-affinity relationships. In an in vitro antitumor assay with seven human tumor cell lines, the bicyclic compounds inhibited selectively the growth of the cell line A427, which is due to induction of apoptosis. In this assay, the compounds behave like the known σ1 receptor antagonist haloperidol.

Synthesis, pharmacological evaluation, and σ1 receptor interaction analysis of hydroxyethyl substituted piperazines

Starting from (S)- or (R)-aspartate, three synthetic strategies were explored to prepare hydroxyethyl substituted piperazines with different substituents at the N-atoms. σ receptor affinity was recorded using receptor material from both animal and human o

Involvement of apoptosis and autophagy in the death of RPMI 8226 multiple myeloma cells by two enantiomeric sigma receptor ligands

Over-expression of σ receptors by many tumor cell lines makes ligands for these receptors attractive as potential chemotherapeutic drugs. Enantiomeric piperazines (S)-4 and (R)-4 were prepared as potential σ-receptor ligands in a chiral pool synthesis starting from (S)- and (R)-aspartate. Both compounds showed high affinities for the σ1 and σ2 receptors. In the human multiple myeloma cell line RPMI 8226, a line expressing high levels of σ receptors, both compounds inhibited cell proliferation with IC50 values in the low μM range. No chiral differentiation between either the σ receptor binding affinity or the cytotoxicity of the two enantiomers was observed. Both compounds induced apoptosis, which was evidenced by nuclear condensation, binding of annexin-V to phosphatidylserine in the outer leaf of the cell membrane, cleavage products of poly(ADP-ribose) polymerase-1 (PARP-1) and caspase-8 as well as the expression of bcl2 family members bax, bad and bid. However, apoptosis appeared to be caspase independent. Increased levels of the phosphorylated form of the microtubule associated protein light chain 3-II (LC3-II), an autophagosome marker, gave evidence that both compounds induced autophagy. However, further data (e.g., treatment with wortmannin) indicate that autophagy is incomplete and not cytoprotective. Lipid peroxidation (LPO) was observed in RPMI 8226 cells treated with the two compounds, and the lipid antioxidant α-tocopherol attenuated LPO. Interestingly, α-tocopherol reduced significantly both apoptosis and autophagy induced by the compounds. These results provide evidence that, by initiating LPO and changes in mitochondrial membrane potential, both compounds induce apoptosis and autophagy in RPMI 8226 cells.