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Cas Database

14358-33-9

14358-33-9

Identification

Synonyms:H-DL-Asp(OMe)-OMe·HCl;Asparticacid, dimethyl ester, hydrochloride (9CI);Aspartic acid, dimethyl ester,hydrochloride, DL- (8CI);DL-Aspartic acid, dimethyl ester, hydrochloride;

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Safety information and MSDS view more

  • Pictogram(s):Xi

  • Hazard Codes:Xi

  • Signal Word:Warning

  • Hazard Statement:H317 May cause an allergic skin reaction

  • First-aid measures: General adviceConsult a physician. Show this safety data sheet to the doctor in attendance.If inhaled If breathed in, move person into fresh air. If not breathing, give artificial respiration. Consult a physician. In case of skin contact Wash off with soap and plenty of water. Consult a physician. In case of eye contact Rinse thoroughly with plenty of water for at least 15 minutes and consult a physician. If swallowed Never give anything by mouth to an unconscious person. Rinse mouth with water. Consult a physician.

  • Fire-fighting measures: Suitable extinguishing media Use water spray, alcohol-resistant foam, dry chemical or carbon dioxide. Wear self-contained breathing apparatus for firefighting if necessary.

  • Accidental release measures: Use personal protective equipment. Avoid dust formation. Avoid breathing vapours, mist or gas. Ensure adequate ventilation. Evacuate personnel to safe areas. Avoid breathing dust. For personal protection see section 8. Prevent further leakage or spillage if safe to do so. Do not let product enter drains. Discharge into the environment must be avoided. Pick up and arrange disposal. Sweep up and shovel. Keep in suitable, closed containers for disposal.

  • Handling and storage: Avoid contact with skin and eyes. Avoid formation of dust and aerosols. Avoid exposure - obtain special instructions before use.Provide appropriate exhaust ventilation at places where dust is formed. For precautions see section 2.2. Store in cool place. Keep container tightly closed in a dry and well-ventilated place.

  • Exposure controls/personal protection:Occupational Exposure limit valuesBiological limit values Handle in accordance with good industrial hygiene and safety practice. Wash hands before breaks and at the end of workday. Eye/face protection Safety glasses with side-shields conforming to EN166. Use equipment for eye protection tested and approved under appropriate government standards such as NIOSH (US) or EN 166(EU). Skin protection Wear impervious clothing. The type of protective equipment must be selected according to the concentration and amount of the dangerous substance at the specific workplace. Handle with gloves. Gloves must be inspected prior to use. Use proper glove removal technique(without touching glove's outer surface) to avoid skin contact with this product. Dispose of contaminated gloves after use in accordance with applicable laws and good laboratory practices. Wash and dry hands. The selected protective gloves have to satisfy the specifications of EU Directive 89/686/EEC and the standard EN 374 derived from it. Respiratory protection Wear dust mask when handling large quantities. Thermal hazards

Supplier and reference price

  • Manufacture/Brand
  • Product Description
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  • Manufacture/Brand:Usbiological
  • Product Description:DL-Aspartic acid dimethyl ester hydrochloride
  • Packaging:10g
  • Price:$ 333
  • Delivery:In stock
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  • Manufacture/Brand:TRC
  • Product Description:Dl-AsparticAcidDimethylEsterHydrochloride
  • Packaging:10g
  • Price:$ 75
  • Delivery:In stock
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  • Manufacture/Brand:Crysdot
  • Product Description:H-DL-Asp(OMe)-OMe.HCl 97%
  • Packaging:500g
  • Price:$ 317
  • Delivery:In stock
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  • Manufacture/Brand:ChemScene
  • Product Description:DL-Asparticaciddimethylesterhydrochloride >97.0%
  • Packaging:500g
  • Price:$ 353
  • Delivery:In stock
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  • Manufacture/Brand:ChemScene
  • Product Description:DL-Asparticaciddimethylesterhydrochloride >97.0%
  • Packaging:100g
  • Price:$ 93
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  • Manufacture/Brand:Chem-Impex
  • Product Description:DL-Aspartic acid dimethyl ester hydrochloride ≥ 98.5% (Assay: Anhydrous basis)
  • Packaging:250G
  • Price:$ 495
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  • Manufacture/Brand:Chem-Impex
  • Product Description:DL-Asparticaciddimethylesterhydrochloride,98.5%(Assay:Anhydrousbasis) 98.5%(Assay:Anhydrousbasis)
  • Packaging:25G
  • Price:$ 78.4
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  • Manufacture/Brand:Chem-Impex
  • Product Description:DL-Asparticaciddimethylesterhydrochloride,98.5%(Assay:Anhydrousbasis) 98.5%(Assay:Anhydrousbasis)
  • Packaging:5G
  • Price:$ 22.4
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  • Manufacture/Brand:Chem-Impex
  • Product Description:DL-Asparticaciddimethylesterhydrochloride,98.5%(Assay:Anhydrousbasis) 98.5%(Assay:Anhydrousbasis)
  • Packaging:100G
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  • Manufacture/Brand:Chemenu
  • Product Description:DL-AsparticAcidDimethylEsterHydrochloride 97%
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Relevant articles and documentsAll total 16 Articles be found

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

Korpis, Katharina,Weber, Frauke,Brune, Stefanie,Wünsch, Bernhard,Bednarski, Patrick J.

, p. 221 - 233 (2014)

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.

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

Chiaramonte, Niccolò,Angeli, Andrea,Sgambellone, Silvia,Bonardi, Alessandro,Nocentini, Alessio,Bartolucci, Gianluca,Braconi, Laura,Dei, Silvia,Lucarini, Laura,Teodori, Elisabetta,Gratteri, Paola,Wünsch, Bernhard,Supuran, Claudiu T.,Romanelli, Maria Novella

, (2021/12/17)

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

Petermichl, Markus,Steinert, Christine,Schobert, Rainer

, p. 730 - 738 (2019/01/23)

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

-

Paragraph 0031; 0032; 0033; 0034, (2019/01/24)

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

-

Paragraph 0045; 0046; 0047; 0048, (2019/01/24)

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

-

Paragraph 0035; 0064; 0065, (2018/04/01)

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.

Process route upstream and downstream products

Process route

dimethyl (S)-malate
617-55-0

dimethyl (S)-malate

dimethyl L-aspartate hydrochloride
32213-95-9

dimethyl L-aspartate hydrochloride

dimethyl (R)-2-aminobutanedioate hydrochloride
14358-33-9,32213-95-9,69630-50-8

dimethyl (R)-2-aminobutanedioate hydrochloride

Conditions
Conditions Yield
Multistep reaction. Title compound not separated from byproducts; e.e. = 95percent;
methanol
67-56-1

methanol

dimethyl (R)-2-aminobutanedioate hydrochloride
14358-33-9,32213-95-9,69630-50-8

dimethyl (R)-2-aminobutanedioate hydrochloride

Conditions
Conditions Yield
With acetyl chloride;
100%
With thionyl chloride; at 0 - 20 ℃; for 16.1667h; Inert atmosphere;
99%
With acetyl chloride; Reflux;
73%
methanol; With thionyl chloride; at 0 ℃; for 0.5h;
(2R)-aspartic acid; Heating;
With thionyl chloride; at 0 - 20 ℃;
With chloro-trimethyl-silane; at 20 ℃; for 16h; Inert atmosphere;
With thionyl chloride; at 20 ℃; for 3.5h; Cooling with ice;
With thionyl chloride; at 0 - 29 ℃; for 30h; Concentration; Temperature;
107.8 g
With hydrogenchloride; thionyl chloride; In water; at 0 - 30 ℃;
With chloro-trimethyl-silane; at 0 - 20 ℃; for 16h; Inert atmosphere;
With thionyl chloride; at 0 - 10 ℃; for 2h; Reflux;
With thionyl chloride; at 0 - 10 ℃; for 2h; Reflux;
With thionyl chloride; at 20 ℃; for 17h; Cooling with ice; Reflux;
chloro-trimethyl-silane
75-77-4

chloro-trimethyl-silane

dimethyl (R)-2-aminobutanedioate hydrochloride
14358-33-9,32213-95-9,69630-50-8

dimethyl (R)-2-aminobutanedioate hydrochloride

Conditions
Conditions Yield
In methanol; at 20 ℃; Cooling;
99.9%
In methanol; at 20 ℃; for 16h; enantioselective reaction; Cooling with ice;
99.9%
benzaldehyde
100-52-7

benzaldehyde

dimethyl (R)-2-aminobutanedioate hydrochloride
14358-33-9,32213-95-9,69630-50-8

dimethyl (R)-2-aminobutanedioate hydrochloride

Dimethyl D-N-benzylaspartate
155069-71-9

Dimethyl D-N-benzylaspartate

Conditions
Conditions Yield
With sodium cyanoborohydride; In methanol; 1.) r.t., 4 h, 2.) 2 h;
83%
benzaldehyde; dimethyl (R)-2-aminobutanedioate hydrochloride; With triethylamine; In methanol; at 10 - 35 ℃; for 1h; pH=7 - Ca. 8; Enzymatic reaction;
With potassium borohydride; water; In methanol; at 0 - 15 ℃; for 1h;
benzaldehyde; dimethyl (R)-2-aminobutanedioate hydrochloride; With triethylamine; In methanol; at 10 - 35 ℃; for 1h; pH=7 - Ca. 8;
With potassium borohydride; water; In methanol; at 0 - 15 ℃; for 1h;
4-Fluorobenzenesulfonyl chloride
349-88-2

4-Fluorobenzenesulfonyl chloride

dimethyl (R)-2-aminobutanedioate hydrochloride
14358-33-9,32213-95-9,69630-50-8

dimethyl (R)-2-aminobutanedioate hydrochloride

dimethyl (2R)-2-[[(4-fluorophenyl)sulfonyl]amino]-butanedioate
1218918-76-3

dimethyl (2R)-2-[[(4-fluorophenyl)sulfonyl]amino]-butanedioate

Conditions
Conditions Yield
With triethylamine; In tetrahydrofuran; at 20 ℃; for 16h; Inert atmosphere;
93%
With triethylamine; In tetrahydrofuran; at 0 - 20 ℃;
dimethyl (R)-2-aminobutanedioate hydrochloride
14358-33-9,32213-95-9,69630-50-8

dimethyl (R)-2-aminobutanedioate hydrochloride

2-nitro-benzaldehyde
552-89-6

2-nitro-benzaldehyde

2-(2-nitrobenzylamino)succinic acid dimethyl ester

2-(2-nitrobenzylamino)succinic acid dimethyl ester

Conditions
Conditions Yield
dimethyl (R)-2-aminobutanedioate hydrochloride; With sodium acetate; In ethanol; for 0.166667h;
2-nitro-benzaldehyde; In ethanol; at 20 ℃; for 1.5h;
With sodium cyanoborohydride; In ethanol; at 20 ℃; for 0.0833333h;
benzyl (2S,4aS,6aS,6bR,8aS,10S,12aS,12bR,14bR)-10-(chlorocarbonyl)-2,4a,6a,6b,9,9,12a-heptamethyl-13-oxo-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,12b,13,14b-icosahydropicene-2-carboxylate

benzyl (2S,4aS,6aS,6bR,8aS,10S,12aS,12bR,14bR)-10-(chlorocarbonyl)-2,4a,6a,6b,9,9,12a-heptamethyl-13-oxo-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,12b,13,14b-icosahydropicene-2-carboxylate

dimethyl (R)-2-aminobutanedioate hydrochloride
14358-33-9,32213-95-9,69630-50-8

dimethyl (R)-2-aminobutanedioate hydrochloride

dimethyl ((3S,4aS,6aR,6bS,8aS,11S,12aR,14aR,14bS)-11-((benzyloxy)carbonyl)4,4,6a,6b,8a,11,14b-heptamethyl-14-oxo-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,14,14a,14b-icosahydropicene-3-carbonyl)-D-aspartate

dimethyl ((3S,4aS,6aR,6bS,8aS,11S,12aR,14aR,14bS)-11-((benzyloxy)carbonyl)4,4,6a,6b,8a,11,14b-heptamethyl-14-oxo-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,14,14a,14b-icosahydropicene-3-carbonyl)-D-aspartate

Conditions
Conditions Yield
With triethylamine; In dichloromethane; at 20 ℃; for 0.5h;
benzaldehyde
100-52-7

benzaldehyde

dimethyl (R)-2-aminobutanedioate hydrochloride
14358-33-9,32213-95-9,69630-50-8

dimethyl (R)-2-aminobutanedioate hydrochloride

C<sub>13</sub>H<sub>15</sub>NO<sub>4</sub>
1584725-20-1

C13H15NO4

Conditions
Conditions Yield
With sodium sulfate; triethylamine; In dichloromethane; at 20 ℃; for 16h;
2.2 g
In dichloromethane; at 20 ℃; for 16h; Inert atmosphere;
1,3,5-benzene tris(carbonyl chloride)
4422-95-1

1,3,5-benzene tris(carbonyl chloride)

dimethyl (R)-2-aminobutanedioate hydrochloride
14358-33-9,32213-95-9,69630-50-8

dimethyl (R)-2-aminobutanedioate hydrochloride

(1R,3R,5RS)-1,3,5-benzenetricarbonyl tri-(R-(D)-aspartic dimethyl ester)

(1R,3R,5RS)-1,3,5-benzenetricarbonyl tri-(R-(D)-aspartic dimethyl ester)

Conditions
Conditions Yield
dimethyl (R)-2-aminobutanedioate hydrochloride; With triethylamine; In dichloromethane; at 0 ℃; for 0.333333h;
1,3,5-benzene tris(carbonyl chloride); In dichloromethane;
85%
dimethyl (R)-2-aminobutanedioate hydrochloride; With triethylamine; In dichloromethane; for 0.166667h;
1,3,5-benzene tris(carbonyl chloride); In dichloromethane; for 24h;
N-(benzyloxycarbonyl)-L-glutamic acid α-tert-butyl ester

N-(benzyloxycarbonyl)-L-glutamic acid α-tert-butyl ester

dimethyl (R)-2-aminobutanedioate hydrochloride
14358-33-9,32213-95-9,69630-50-8

dimethyl (R)-2-aminobutanedioate hydrochloride

isobutyl chloroformate
543-27-1

isobutyl chloroformate

dimethyl N-[4-(benzyloxycarbonylamino)-4-tert.-butoxycarbonylbutanoyl]-D-aspartate

dimethyl N-[4-(benzyloxycarbonylamino)-4-tert.-butoxycarbonylbutanoyl]-D-aspartate

Conditions
Conditions Yield
With triethylamine; In dichloromethane;
1.93 g (75%)
With triethylamine; In dichloromethane;
1.93 g (75%)

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