3619-02-1

Basic information

• Product Name: AC-ALA-OME
• Synonyms: N-Acetyl-L-alanine methyl ester;N-ALPHA-ACETYL-L-ALANINE METHYL ESTER;AC-ALANINE-OME;AC-ALA-OME;ACETYL-L-ALANINE METHYL ESTER;Ac-L-Ala-OMe;N-alpha-Actetyl-L-alanine methyl ester;(2S)-2-(Acetylamino)propanoic acid methyl ester
• CAS NO: 3619-02-1
• Molecular Formula: C₆H₁₁NO₃
• Molecular Weight: 145.16
• Mol File: 3619-02-1.mol

Chemical Properties

• Boiling Point: 251.1oC at 760 mmHg
• Flash Point: 105.7oC
• Appearance: Yellow/Liquid
• Density: 1.056g/cm3
• Vapor Pressure: 0.0209mmHg at 25°C
• Refractive Index: 1.426
• Storage Temp.: Store at RT.
• PKA: 14.78±0.46(Predicted)
• CAS DataBase Reference: AC-ALA-OME(CAS DataBase Reference)
• NIST Chemistry Reference: AC-ALA-OME(3619-02-1)
• EPA Substance Registry System: AC-ALA-OME(3619-02-1)

Safety Data

• Hazardous Substances Data: 3619-02-1(Hazardous Substances Data)

Usage

Chemical Properties

Yellow liquid

InChI:InChI=1/C6H11NO3/c1-4(6(9)10-3)7-5(2)8/h4H,1-3H3,(H,7,8)/t4-/m0/s1

Upstream product

• 186581-53-3 diazomethane 
• 5429-56-1 N-Acetamidoacrylic acid 
• 35356-70-8 Methyl 2-acetamidoacrylate 
• 10065-72-2 L-Alanine methyl ester 
• 830-03-5 4-nitrophenol acetate 
• 67-56-1 methanol 
• 1417912-28-7 C₁₀H₁₅NO₃ 
• 21622-00-4 Cyclopent-3-ene-1,1-dicarboxylic acid diethyl ester 
• 7652-46-2 Ac-Cys-OMe 
• 177750-09-3 N-(1-(4-(trifluoromethyl)phenyl)vinyl)acetamide 
• 26629-33-4 methyl 2-acetamidopropanoate 

Downstream Products

• 19701-83-8 N-acetyl-N'-methyl-L-alanylamide 
• 372-48-5 2-fluoropyridine 
• 88001-11-0 C₆H₁₂NO₃⁽¹⁺⁾ 
• 372-47-4 3-Fluoropyridine 
• 74-89-5 methylamine 
• 464-72-2 tetraphenylethane-1,2-diol 
• 56-41-7 L-alanin 
• 97-69-8 (S)-acetamidoalanine 
• 116287-43-5 N-thioacetyl-L-alanine methyl ester 
• 600-22-6 pyruvic acid methyl ester 

Relevant articles and documents

Microwave-assisted cleavage of cysteine perfluoroaryl thioethers

The cysteine- perfluoroarene SNAr reaction allows for the sequence-specific attachment of dyes and affinity tags to peptides and proteins. However, while many methods exist for the desulfuration of native and functionalized cysteine residues, there are no reports of their application to perfluoroarylated cysteines. Herein we report both the hydrogenolysis of a perfluoroarylated cysteine to alanine and elimination to dehydroalanine, reactions that are both accelerated by microwave irradiation.

Mechanistically Guided One Pot Synthesis of Phosphine-Phosphite and Its Implication in Asymmetric Hydrogenation

Although hybrid bidentate ligands are known to yield highly enantioselective products in asymmetric hydrogenation (AH), synthesis of these ligands is an arduous process. Herein, a one pot, atom-economic synthesis of a hybrid phosphine-phosphite (L1) is reported. After understanding the reactivity difference between an O-nucleophile versus C-nucleophile, one pot synthesis of Senphos (L1) was achieved (72 %). When L1 was treated with [Rh], 31P NMR revealed bidentate coordination to Rh. Senphos, in the presence of rhodium, catalyzes the AH of Methyl-2-acetamido-3-phenylacrylate and discloses an unprecedented turn over frequency of 2289, along with excellent enantio-selectivity (92 %). The generality is demonstrated by hydrogenating an array of alkenes. The AH operates under mild conditions of 1–2 bar H2 pressure, at room temperature. The practical relevance of L1 is demonstrated by scaling-up the reaction to 1 g and by synthesizing DOPA, a drug widely employed for the treatment of Parkinson's disease. Computational insights indicate that the R isomer is preferred by 3.8 kcal/mol over the S isomer.

2-(1S)-Camphanoyloxy-2′-phosphanylbiphenyl Ligands – Synthesis, Structure, and Preliminary Tests in Transition-Metal Catalysis

Diastereoisomer separation of the (1S)-camphanic acid 2-isopropylphenylphosphanyl-phenyl ester 1 exemplifies the potential of (1S)-camphanoyl chloride for enantiomer separation of hydroxyl-functional asymmetric phosphanes. Esterification of lithium 2′-phosphanylbiphenyl-2-olates, generated from the respective 2-OH or 2-OSiMe3 precursors 2aOH and 2b–fSi, furnished the 2-(1S)-camphanoyloxy-biphenylphosphanes 3a–c as 1:1 mixtures of diastereomers with low barriers for interconversion by rotation around the C–C axis (ΔG# = 70–73 kJ mol–1 for 3a and 3c by 31P VT NMR spectroscopy). The P-asymmetric compounds 3d–f form 1:1 mixtures of stereoisomers. There is a tendency to cocrystallization of two preferred diastereoisomers, as shown by the crystal structure analyses of 3dD and 3fD, and in solution, there is a tendency toward partial isomerization to the sterically less-favored atropisomers. The [RhCl(cod)(3dD)] complex 4dD, however, seems stable in solution. Excess 2dLi reacted with (1S)-camphanoyl chloride preferentially to form the (SP,Rax,1S) isomer, which was separated by crystallization as enantiopure 3dE, characterized by single-crystal XRD. Preliminary screening tests of this ligand in Rh-catalyzed asymmetric hydrogenations of N-(1-phenylvinyl)acetamide allowed high conversion and up to 59 % ee. Hydrosilylation of acetophenone proceeded with 78 % conversion and 48 % ee; Suzuki–Miyaura couplings of 1-bromo-2-naphthol with PhB(OH)2, in the presence of 3b/[Pd(OAc)2], gave yields up to 98 %.

Dual-pathway chain-end modification of RAFT polymers using visible light and metal-free conditions

We report a metal-free strategy for the chain-end modification of RAFT polymers utilizing visible light. By turning the light source on or off, the reaction pathway in one pot can be switched between either complete desulfurization (hydrogen chain-end) or simple cleavage (thiol chain-end), respectively. The versatility of this process is exemplified by application to a wide range of polymer backbones under mild, quantitative conditions using commercial reagents.

Assisted Tandem Catalysis: Metathesis Followed by Asymmetric Hydrogenation from a Single Ruthenium Source

Here we report the first example of a tandem metathesis-asymmetric hydrogenation protocol where the prochiral olefin generated by metathesis is hydrogenated with high enantioselectivity by an in situ formed chiral ruthenium catalyst. We show that either the ruthenium metathesis catalysts or the ruthenium species formed during the metathesis reaction can be converted into an efficient asymmetric hydrogenation catalyst upon addition of a chiral ligand and an alcohol. The performance in asymmetric hydrogenation appears to be very dependent on the solvent, the chiral ligand, and the prochiral substrate.

P-CHIROGENIC ORGANOPHOSPHORUS COMPOUNDS

The present invention relates to novel P-chirogenic organophosphorus compounds of general formula (I). The present invention also provides a process for the synthesis of said compounds of formula (I). The present invention also relates to intermediate products of general formulae (II), (III) and (IV), as shown below, which are involved in the synthesis of compounds (I). Further, the invention relates to metal complexes comprising compounds (I) as ligands. The novel compounds and complexes of the present invention are useful in asymmetric catalysis by transition metal complexes or organocatalysis, especially for asymmetric hydrogenation or allylation. Compounds of general formula (I) may useful as agrochemical and therapeutic substances, or as reagents or intermediates for fine chemistry.

DIPHOSPHINES AND METAL COMPLEXES

Compounds of the formulae (I) and (II), or a mixture of these enantiomers, where R'1 is C1-C4-alkyl and n is 0, 1 or 2; R1 is C1-C8-alkyl, C2-C8-alken-1-yl, -CH2-OR or - CH2-NR5R6; the two radicals R2 are identical or different and are each hydrogen or a monovalent radical of an electrophilic organic compound, or one R2 has this meaning and the other R2 is hydrogen; sec-phos is a secondary phosphino group; R is C1-C8- alkyl and R5 and R6 are each C1-C6-alkyl or R5 and R6 together form tetramethylene, pentamethylene or 3-oxa-1,5-pentylene, are ligands for metal complexes which can be used as valuable homogeneous catalysts for asymmetric syntheses. The compounds are obtained by a novel process in which 3,3'-metallated 1,1'-di-R1-2,2'- dibromoferrocenes are firstly reacted with sec-phos halide, the bromine atoms are then replaced by lithium and the substituent R2 is subsequently introduced by reaction with an electrophilic organic compound or with water.

Highly enantioselective Rh-catalyzed hydrogenations with heterocombinations of pentafluorobenzyl- and methoxybenzyl-derived binaphthyl phosphites

The Rh-catalyzed hydrogenations of dimethyl itaconate and methyl acetamido acrylate using selected heterocombinations of pentafluorobenzyl- and methoxybenzyl-derived binaphthyl phosphites proved to be highly enantioselective (ee 93-99%). In these selected

UREAphos: Supramolecular bidentate ligands for asymmetric hydrogenation

Supramolecular bidentate phosphite ligands are presented as a new class of ligands for rhodium catalysed asymmetric hydrogenation. The Royal Society of Chemistry.

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