19914-36-4

Basic information

• Product Name: AC-D-ALA-OME
• Synonyms: ACETYL-D-ALANINE METHYL ESTER;AC-D-ALANINE-OME;AC-D-ALA-OME;N-ALPHA-ACETYL-D-ALANINE METHYL ESTER;N-alpha-Actetyl-D-alanine methyl ester;(2R)-2-(Acetylamino)propanoic acid methyl ester;(2R)-2-(Acetylamino)propionic acid methyl ester;(R)-2-(Acetylamino)propanoic acid methyl ester
• CAS NO: 19914-36-4
• Molecular Formula: C₆H₁₁NO₃
• Molecular Weight: 145.16
• Product Categories: Amino Acid Derivatives;Amino Acids
• Mol File: 19914-36-4.mol

Chemical Properties

• Boiling Point: 251.1℃
• Flash Point: 105.7℃
• Appearance: /
• Density: 1.056
• Storage Temp.: 2-8°C
• PKA: 14.78±0.46(Predicted)
• CAS DataBase Reference: AC-D-ALA-OME(CAS DataBase Reference)
• NIST Chemistry Reference: AC-D-ALA-OME(19914-36-4)
• EPA Substance Registry System: AC-D-ALA-OME(19914-36-4)

Safety Data

• Hazardous Substances Data: 19914-36-4(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
AC-D-ALA-OME is used as a catalyst in the preparation of chiral bis(phospholate)-rhodium complexes for asymmetric hydrogenation. This application is significant in the synthesis of enantiomerically pure compounds, which are essential in the development of pharmaceuticals with improved efficacy and reduced side effects.
Used in Chemical Synthesis:
AC-D-ALA-OME is used as a key intermediate in the synthesis of various chiral compounds, which are crucial in the development of new drugs and materials with specific properties. Its role in asymmetric hydrogenation allows for the creation of enantiomerically pure products, enhancing the selectivity and efficiency of chemical reactions.
Used in Catalyst Development:
AC-D-ALA-OME is utilized in the development of new catalysts for various chemical reactions, particularly those involving asymmetric hydrogenation. These catalysts are vital in the production of chiral compounds with high enantioselectivity, which are essential in the pharmaceutical, agrochemical, and fine chemical industries.

Upstream product

• 124-41-4 sodium methylate 
• 14316-06-4 D-alanine methyl ester hydrochloride 
• 75-36-5 acetyl chloride 
• 186581-53-3 diazomethane 
• 5429-56-1 N-Acetamidoacrylic acid 
• 26629-33-4 methyl 2-acetamidopropanoate 
• 35356-70-8 Methyl 2-acetamidoacrylate 
• 7625-53-8 D-alanine methyl ester 
• 830-03-5 4-nitrophenol acetate 
• 67-56-1 methanol 
• 19436-52-3 (R)-2-(acetylamino)propanoic acid 
• 18107-18-1 diazomethyl-trimethyl-silane 
• 52386-78-4 N-acetyl dehydrophenylalanine methyl ester 
• 57294-56-1 methyl α-N-(acetylamino)acrylate 

Relevant articles and documents

Chiral phosphite-phosphoroamidites: A new class of ligand for asymmetric catalytic hydrogenation

A series of novel phosphite-phosphoroamidite ligands, derived from readily available D-xylose, has been used for the first time in the asymmetric Rh-catalyzed hydrogenation of a series of α,β-unsaturated carboxylic acid derivatives with excellent enantios

Heterogenization of Rh-MeDuPHOS by occlusion in polyvinyl alcohol films

A new recyclable chiral heterogeneous catalytic system was obtained by the occlusion of Rh-MeDuPHOS in polyvinyl alcohol film. Enantiomeric excess of up to 96% was achieved in the asymmetric hydrogenation of methyl 2-acetamidoacrylate in aqueous medium.

Kinetic resolution of N-acetyl-DL-alanine methyl ester using immobilized Escherichia coli cells bearing recombinant esterase from Bacillus cereus

D-alanine is widely used in medicine, food, additives, cosmetics, and other consumer items. Esterase derived from Bacillus cereus WZZ001 exhibits high hydrolytic activity and stereoselectivity. In this study, we expressed the esterase gene in Escherichia coli BL21 (DE3). We analyzed the biocatalytic resolution of N-acetyl-DL-alanine methyl ester by immobilized whole E.?coli BL21 (DE3) cells, which were prepared through embedding and cross-linking. We analyzed biocatalytic resolution under the optimal conditions of pH of 7.0, temperature of 40°C and substrate concentration of at 700?mM with an enantiomeric excess of 99.99% and e.e.p of 99.50%. The immobilized recombinant B.?cereus esterase E.?coli BL21 (DE3) cells exhibited excellent reusability and retained 86.04% of their initial activity after 15 cycles of repeated reactions. The immobilized cells are efficient and stable biocatalysts for the preparation of N-acetyl-D-alanine methyl esters.

Enantioselective hydrogenation of polar substrates in inverted supercritical CO2/aqueous biphasic media

An inverted supercritical CO2/aqueous biphasic catalytic system allows highly enandoselective hydrogenation of polar water-soluble substrates and efficient recycling of the CO2-philic catalysts. The Royal Society of Chemistry 2005.

Directed evolution of enantioselective hybrid catalysts: a novel concept in asymmetric catalysis

The concept of directed evolution of enantioselective hybrid catalysts was proposed in 2001/2002 and implemented experimentally for the first time in a proof-of-concept study in 2006. The idea is based on directed evolution, which comprises repeating cycl

Unsymmetrical P-chirogenic bis(phosphane) ligands: Their preparation and use in rhodium-catalyzed asymmetric hydrogenation

A series of bis(phosphanes) (SP,SP′)-R1(Me)PCH2 CH2P′R2R3 (1a-k; R1, R2, and R3 = 1-adamantyl, tert-butyl, cyclohexyl, cyclopentyl, isopropyl, methyl, phenyl; abbreviated as unsymmetrical BisP*) has successfully been synthesized, by coupling of the (RP)-configured tosylates 5a-d or mesylates 6a-g with lithiated (SP)-R1 (Me)PH-BH3 adducts. Asymmetric hydrogenations catalyzed by rhodium complexes of the unsymmetrical BisP* moieties as ligands revealed extremely high enantioselectivities - 99% (9b) and 98% (9e) - when the trisubstituted and tetrasubstituted dehydro-α-amino acid derivatives 8b and 8e, respectively, were used as substrates. It was found that unsymmetrical BisP* species tended to exhibit higher enantioselectivity than C2-symmetrical BisP* species in the Rh-catalyzed hydrogenation of (Z)-dehydro-β-amino acid and enamide derivatives. These results implied that the differentiation between the chiral environments at the two phosphorus atoms could effectively achieve higher enantioselectivity. For each substrate, moreover, it was possible to improve the enantioselectivity by changing the combination of substituents on the two phosphorus atoms. Wiley-VCH Verlag GmbH, 69451 Weinheim, Germany, 2002.

Synthesis and application of C2-symmetric diamino FERRIPHOS as ligands for enantioselective Rh-catalyzed preparation of chiral α-amino acids

C2-Symmetrical ferrocenyl diamino diphosphines (diamino FERRIPHOS ligands) proved to be excellent ligands for the rhodium-catalyzed enantioselective reduction of methyl α-acetamidoacrylates. The straightforward synthesis, their air stability an

A novel system consisting of Rh-DuPHOS and ionic liquid for asymmetric hydrogenations

The ionic liquid [bmim][PF6] was found to provide extra stability to the air-sensitive chiral catalyst Rh-MeDuPHOS in asymmetric hydrogenation of enamides.

Chiral phosphine-phosphite ligands in the highly enantioselective rhodium-catalyzed asymmetric hydrogenation

We have investigated a series of enantiopure phosphine-phosphite ligands (P1-P2 = ligands 1-4) in the rhodium-catalyzed asymmetric hydrogenation reaction. Intermediate [Rh(P1-P2)(cod)]BF4 and [Rh(Psu

Directed evolution of hybrid enzymes: Evolving enantioselectivity of an achiral Rh-complex anchored to a protein

The concept of utilizing the methods of directed evolution for tuning the enantioselectivity of synthetic achiral metal-ligand centers anchored to proteins has been implemented experimentally for the first time. The Royal Society of Chemistry 2006.