(R)-Methyl 2-acetamidopropanoate

Base Information

• Chemical Name: (R)-Methyl 2-acetamidopropanoate
• CAS No.: 19914-36-4
• Molecular Formula: C6H11 N O3
• Molecular Weight: 145.158
• Hs Code.: 2924199090
• European Community (EC) Number: 890-053-3
• DSSTox Substance ID: DTXSID20426223
• Nikkaji Number: J411.697F
• Wikidata: Q63392860
• Mol file: 19914-36-4.mol

Synonyms:(R)-Methyl 2-acetamidopropanoate;19914-36-4;Ac-d-ala-ome;methyl (2R)-2-acetamidopropanoate;Acetyl-D-alanine methyl ester;D-Alanine, N-acetyl-, methyl ester;N-Acetyl-D-alanine methyl;SCHEMBL1884920;DTXSID20426223;(R)-N-acetylalanine methyl ester;D-Alanine,N-acetyl-,methyl ester;FQGVVDYNRHNTCK-SCSAIBSYSA-N;N-ACETYL-ALANINE METHYLESTER;MFCD00080822;AKOS016843112;FD21104;DS-15980;CS-0158251;(R)-2-Acetylamino-propionic acid methyl ester;J-012869;Q63392860;N-alpha-Acetyl-D-alanine methyl ester (Ac-D-Ala-OMe)

Chemical Property of (R)-Methyl 2-acetamidopropanoate

Chemical Property:

• Boiling Point: 251.1℃
• PKA: 14.78±0.46(Predicted)
• Flash Point: 105.7℃
• PSA: 55.40000
• Density: 1.056
• LogP: 0.07490
• Storage Temp.: 2-8°C
• XLogP3: -0.6
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 3
• Exact Mass: 145.07389321
• Heavy Atom Count: 10
• Complexity: 144

Purity/Quality:

99.3% ^*data from raw suppliers

N-Acetyl-D-alanine Methyl Ester ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C(=O)OC)NC(=O)C
• Isomeric SMILES: C[C@H](C(=O)OC)NC(=O)C
• Uses: N-Acetyl-D-alanine Methyl Ester was used in preparation of chiral bis(phospholate)-rhodium complexesa s catalysts via asymmetric hydrogentation.

Technology Process of (R)-Methyl 2-acetamidopropanoate

There total 20 articles about (R)-Methyl 2-acetamidopropanoate which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 100.0%

Methyl 2-acetamidoacrylate (35356-70-8) → Methyl (R)-N-acetylalaninate (19914-36-4)

Guidance literature:

With {(1,5-cyclooctadiene)Rh(1,2-bis((2R,5R)-2,5-diethylphospholano)benzene)}triflate; hydrogen; In methanol; at 20 - 25 ℃; under 1551.4 Torr;

Reference yield: 100.0%

Methyl 2-acetamidoacrylate (35356-70-8) → (S)-N-acetylalanine methyl ester (3619-02-1) + Methyl (R)-N-acetylalaninate (19914-36-4)

Guidance literature:

With hydrogen; rhodium(I)-bis(1,5-cyclooctadiene) tetrafluoroborate; (2R,2'R)-bis(diphenylphosphino)-(1R,1'R)-dicyclopentane; In tetrahydrofuran; at 20 ℃; for 24h; under 750.075 Torr;

Reference yield:

D-alanine methyl ester (7625-53-8,10065-72-2,21705-13-5) + 4-nitrophenol acetate (830-03-5) → 4-nitro-phenol (100-02-7,78813-13-5,89830-32-0) + Methyl (R)-N-acetylalaninate (19914-36-4)

Guidance literature:

β‐cyclodextrin; In water; dimethyl sulfoxide; at 25 ℃; Rate constant; Mechanism;

upstream raw materials:

sodium methylate

D-alanine methyl ester hydrochloride

acetyl chloride

diazomethane

Refernces

• 1、 Wolfson, Adi,Geresh, Shimona,Gottlieb, Moshe,Herskowitz, Moti. "Heterogenization of Rh-MeDuPHOS by occlusion in polyvinyl alcohol films". . p. 465 - 468. Retrieved 2002.
• 2、 Burgemeister, Katja,Francio, Giancarlo,Hugl, Herbert,Leitner, Walter. "Enantioselective hydrogenation of polar substrates in inverted supercritical CO2/aqueous biphasic media". . p. 6026 - 6028. Retrieved 2005.
• 3、 Ohashi, Atsushi,Kikuchi, Shin-Ichi,Yasutake, Masaya,Imamoto, Tsuneo. "Unsymmetrical P-chirogenic bis(phosphane) ligands: Their preparation and use in rhodium-catalyzed asymmetric hydrogenation". . p. 2535 - 2546. Retrieved 2002.
• 4、 Guernik,Wolfson,Herskowitz,Greenspoon,Geresh. "A novel system consisting of Rh-DuPHOS and ionic liquid for asymmetric hydrogenations". . p. 2314 - 2315. Retrieved 2001.
• 5、 Reetz, Manfred T.,Peyralans, Jerome J.-P.,Maichele, Andrea,Fu, Yu,Maywald, Matthias. "Directed evolution of hybrid enzymes: Evolving enantioselectivity of an achiral Rh-complex anchored to a protein". . p. 4318 - 4320. Retrieved 2006.
• 6、 Burk, Mark J.,Feng, Shaoguang,Gross, Michael F.,Tumas, William. "Asymmetric catalytic hydrogenation reactions in supercritical carbon dioxide". . p. 8277 - 8278. Retrieved 1995.
• 7、 Junge, Kathrin,Oehme, Günther,Monsees, Axel,Riermeier, Thomas,Dingerdissen, Uwe,Beller, Matthias. "Synthesis of new chiral monodentate aminophosphinites and their use in catalytic asymmetric hydrogenations". . p. 91 - 96. Retrieved 2003.
• 8、 Sugiya, Masashi,Nohira, Hiroyuki. "Synthesis of optically pure bisphosphine oxides and related compounds". . p. 705 - 712. Retrieved 2000.
• 9、 Wolfson, Adi,Janssens, Sofie,Vankelecom, Ivo,Geresh, Shimona,Gottlieb, Moshe,Herskowitz, Moti. "Aqueous enantioselective hydrogenation of methyl 2-acetamidoacrylate with Rh-MeduPHOS occluded in PDMS". . p. 388 - 389. Retrieved 2002.
• 10、 Imamoto, Tsuneo,Oohara, Nobuhiko,Takahashi, Hidetoshi. "Optically active 1,1′-Di-tert-butyl-2,2′-diphosphetanyl and its application in rhodium-catalyzed asymmetric hydrogenations". . p. 1353 - 1358. Retrieved 2004.