40149-67-5

Basic information

• Product Name: dimethyl DL-aspartate
• Synonyms: dimethyl DL-aspartate;Aspartic acid, 1,4-dimethyl ester;DL-Aspartic acid dimethyl;rac-(2R*)-2-Aminosuccinic acid dimethyl ester;DL-Aspartic acid, 1,4-diMethyl ester
• CAS NO: 40149-67-5
• Molecular Formula: C₆H₁₁NO₄
• Molecular Weight: 161.15584
• EINECS: 254-813-2
• Mol File: 40149-67-5.mol

Chemical Properties

• Boiling Point: 223°Cat760mmHg
• Flash Point: 88.9°C
• Appearance: /
• Density: 1.162g/cm³
• CAS DataBase Reference: dimethyl DL-aspartate(CAS DataBase Reference)
• NIST Chemistry Reference: dimethyl DL-aspartate(40149-67-5)
• EPA Substance Registry System: dimethyl DL-aspartate(40149-67-5)

Safety Data

• Hazardous Substances Data: 40149-67-5(Hazardous Substances Data)

Usage

InChI:InChI=1S/C6H11NO4/c1-10-5(8)3-4(7)6(9)11-2/h4H,3,7H2,1-2H3

Upstream product

• 67-56-1 methanol 
• 70-47-3 L-asparagine 
• 36875-41-9 (Z) dimethyl azidoethylenedicarboxylate 
• 28081-31-4 dimethyl α-nitrosuccinate 
• 617-45-8 aspartic Acid 
• 3130-87-8 DL-asparagine monohydrate 
• 762-42-5 dimethyl acetylenedicarboxylate 
• 142026-01-5 (R)-dimethyl 2-azidosuccinate 
• 1783-96-6 (2R)-aspartic acid 
• 617-55-0 dimethyl (S)-malate 
• 130608-05-8 (S)-dimethyl 2-((p-nitrobenzene)sulfonyl)oxy succinate 
• 65414-78-0 (R)-Aspartate α-methyl ester 

Downstream Products

• 6437-34-9 (3,6-dioxo-piperazine-2,5-diyl)-bis-acetic acid dimethyl ester 
• 102017-82-3 N-(4,4'-Nitro-phenylazobenzoyl)-asparaginsaeure-methylester 
• 111971-01-8 C₁₄H₁₅N₃O₅ 
• 77119-27-8 2-[(1-Benzyl-aziridine-2-carbonyl)-amino]-succinic acid dimethyl ester 
• 28081-31-4 dimethyl α-nitrosuccinate 
• 31947-19-0 Dimethyl-benzyloxycarbonyl-sarcosylaspartat 
• 6384-18-5 dimethyl D-aspartate 
• 111971-09-6 3-benzyl-6-carbomethoxy-2,4-dioxo-1,2,3,4-tetrahydropyrimidine 
• 111971-08-5 3-benzyl-6-(methoxycarbonyl)-2-ureido-4-oxo-3,4-dihydropyrimidine 
• 86555-45-5 rac-dimethyl 2-benzamidosuccinate 
• 53880-83-4 N-benzyloxycarbonylglycyl-L-α-aspartic acid dimethyl ester 

Relevant articles and documents

A Concise Asymmetric Route to Nuphar Alkaloids. A Formal Synthesis of (-)-Deoxynupharidine

(Equation presented) A stereocontrolled route to Nuphar alkaloids is described that employs a formal [3 + 3] cycloaddition strategy to assemble the piperidine nucleus. The addition of Pd-TMM complexes to aziridine 10 was found to be sluggish; however, the addition of a functionalized allyl Grignard reagent followed by a Mitsunobu condensation reaction provided 11 in high yield. The employment of this route in the formal synthesis of (-)-deoxynupharidine 1 is described.

Enzymatic methods for the preparation of enantiopure malic and aspartic acid derivatives in organic solvents

The kinetic resolution of malic and aspartic acid diesters as well as of its N-butanoyl dimethyl ester by highly regioselective lipases and acylase I enzymes were studied. Candida antarctica lipase A on Celite catalyzed the enantioselective acylation of the hydroxyl and amino groups. Acylase I from Aspergillus melleus and Candida antarctica lipase B catalyzed the enantioselective alcoholyses of the ester groups at the α- and β-positions, respectively. (C) 1999 Elsevier Science Ltd.

N-Pyrazinoyl substituted amino acids as potential antimycobacterial agents-the synthesis and biological evaluation of enantiomers

Tuberculosis is an infectious disease caused by Mycobacterium tuberculosis (Mtb), each year causing millions of deaths. In this article, we present the synthesis and biological evaluations of new potential antimycobacterial compounds containing a fragment of the first-line antitubercular drug pyrazinamide (PZA), coupled with methyl or ethyl esters of selected amino acids. The antimicrobial activity was evaluated on a variety of (myco)bacterial strains, including Mtb H37Ra, M. smegmatis, M. aurum, Staphylococcus aureus, Pseudomonas aeruginosa, and fungal strains, including Candida albicans and Aspergillus flavus. Emphasis was placed on the comparison of enantiomer activities. None of the synthesized compounds showed any significant activity against fungal strains, and their antibacterial activities were also low, the best minimum inhibitory concentration (MIC) value was 31.25 μM. However, several compounds presented high activity against Mtb. Overall, higher activity was seen in derivatives containing l-amino acids. Similarly, the activity seems tied to the more lipophilic compounds. The most active derivative contained phenylglycine moiety (PC-d/l-Pgl-Me, MIC 1.95 μg/mL). All active compounds possessed low cytotoxicity and good selectivity towards Mtb. To the best of our knowledge, this is the first study comparing the activities of the d- and l-amino acid derivatives of pyrazinamide as potential antimycobacterial compounds.

β-Hydroxy- A nd β-Aminophosphonate Acyclonucleosides as Potent Inhibitors of Plasmodium falciparum Growth

Malaria is an infectious disease caused by a parasite of the genus Plasmodium, and the emergence of parasites resistant to all current antimalarial drugs highlights the urgency of having new classes of molecules. We developed an effective method for the synthesis of a series of β-modified acyclonucleoside phosphonate (ANP) derivatives, using commercially available and inexpensive materials (i.e., aspartic acid and purine heterocycles). Their biological evaluation in cell culture experiments and SAR revealed that the compounds' effectiveness depends on the presence of a hydroxyl group, the chain length (four carbons), and the nature of the nucleobase (guanine). The most active derivative inhibits the growth of Plasmodium falcIParum in vitro in the nanomolar range (IC50 = 74 nM) with high selectivity index (SI > 1350). This compound also showed remarkable in vivo activity in P. berghei-infected mice (ED50 ～0.5 mg/kg) when administered by the IP route and is, although less efficient, still active via the oral route. It is the first ANP derivative with such potent antimalarial activity and therefore has considerable potential for development as a new antimalarial drug.

Stereoselective synthesis of conformationally restricted KOR agonists based on the 2,5-diazabicyclo[2.2.2]octane scaffold

It has been postulated that the KOR affinity depends on the dihedral angle of the ethylenediamine pharmacophore. Herein, 2,5-diazabicyclooctanes bearing a pyrrolidino moiety in the 7-position were envisaged to study KOR agonists with a conformationally rigid ethylenediamine pharmacophore and thus a defined N(pyrrolidine)-C7-C1-N2 dihedral angle. The first approach with an intramolecular addition at the chiral sulfinylimines 9 failed to give bicyclic products. The key step in the second approach was a Dieckmann analogous cyclization providing mixed methyl silyl ketals 11a-e as key intermediates. The highest KOR affinity was found for the 2,5-dibenzyl substituted derivatives (S,R,S)-16a (Ki = 31 nM) and (R,S,R)-16a (Ki = 74 nM) with the pyrrolidine ring oriented towards N-5. The high KOR affinity of (S,R,S)-16a is unexpected, since the KOR pharmacophoric ethylenediamine system adopts a dihedral angle of about 160°, which is quite different from the angle of the energetically most favored conformer of the flexible and potent KOR agonist 2. (S,R,S)-16a represents a KOR agonist with moderate selectivity over MOR (8-fold) and DOR (5-fold), but high selectivity over both σ receptor subtypes. In the [35S]GTPγS assay (S,R,S)-16a reacted as a full KOR agonist with an EC50 value of 240 nM.

D-asparaginic acid preparation method

The invention discloses a D-asparaginic acid preparation method. The configuration inversion technology is adopted, and the preparation method comprises the steps that L-dimethyl malate-2-besilate can be formed by generating L-dimethyl malate through L-malic acid and then making the L-dimethyl malate react with benzene sulfonyl chloride, then the L-dimethyl malate-2-besilate is made to react with phthalimide potassium, and benzenesulfonic acid serves as a good removal agent, so that D- dimethyl aspartate-2-phthalimide is formed, hydrolysis is conducted under the alkaline condition, D-disodium aspartate is generated, after passing through cation exchange resin, effluent is subjected to concentration, and ethyl alcohol with the concentration being 95% is added for crystallization, so that D-asparaginic acid is obtained. By means of the method, neither high temperature nor high pressure is needed, resolution is not needed, environmental pollution is not caused, and the yield can reach 75% and above.

A kind of optical active pharmaceutical process for the preparation of intermediates

The invention relates to a preparation method of an optical active compound, represented by formula I, or a hydrochloride of the optical active compound by taking a compound with optical activity as a starting material. Raw materials of the preparation method are cheap and easily available; no splitting is needed; the whole technological operation is simple and convenient; cost is low; pollution on environment is less; and the preparation method is suitable for industrialized production. In the formula I, n is 1 or 2 or 3.

Azaindoles as potent CRTH2 receptor antagonists

A new class of 7-azaindole analogs of MK-7246 as potent and selective CRTH2 antagonists is reported. The SAR leading to the identification of the optimal azaindole regioisomer as well as the pharmacokinetics and off-target activities of the most potent antagonists are disclosed.

Discovery of MK-7246, a selective CRTH2 antagonist for the treatment of respiratory diseases

In this manuscript we wish to report the discovery of MK-7246 (4), a potent and selective CRTH2 (DP2) antagonist. SAR studies leading to MK-7246 along with two synthetic sequences enabling the preparation of this novel class of CRTH2 antagonist are reported. Finally, the pharmacokinetic and metabolic profile of MK-7246 is disclosed.

An efficient approach to 2-substituted N-tosylpiperdines: asymmetric synthesis of 2-(2-hydroxy substituted)piperidine alkaloids

We have developed an efficient and a general approach to chiral 2-substituted N-tosylpiperidines starting from chiral α-substituted-N-tosylaziridines. Using this approach, we have synthesized (+)-coniine. The synthesis of chiral N-tosyl-2-piperidinylethanol 15 and ent-15, was achieved from l- and d-aspartic acids, respectively in few steps. Piperidine 15 was converted into 2-(2-hydroxysubstituted)piperidines of type 2 in optically active form. By applying this strategy, asymmetric syntheses of halosaline (R,R)-2a, (+)- and (-)-sedamine 2b, (+)- and (-)-allosedamine 2c, (+)- and (-)-sedridine 2d, (+)- and (-)-allosedridine 2e, (+)-tetraponerine T-3 3a, T-4 3c, T-7 3b, and T-8 3d have been achieved in high yields. These stereoisomers can be interconverted via Mitsunobu inversion in excellent yields.