83670-53-5

Basic information

• Product Name: Acetic acid, [[(4-methylphenyl)sulfonyl]imino]-, ethyl ester
• Synonyms: CH27489 ETHYL N-(P-TOLUENESULFONYL)IMINOACETATE;ethyl 4-toluenesulfonyliminoacetate;ethyl N-tosyliminoacetate;N-Tosylimino glyoxylate ethyl ester;(E)-ethyl 2-(tosylimino)acetate
• CAS NO: 83670-53-5
• Molecular Formula: C11H13NO4S
• Molecular Weight: 255.295
• Mol File: 83670-53-5.mol

Chemical Properties

• CAS DataBase Reference: Acetic acid, [[(4-methylphenyl)sulfonyl]imino]-, ethyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: Acetic acid, [[(4-methylphenyl)sulfonyl]imino]-, ethyl ester(83670-53-5)
• EPA Substance Registry System: Acetic acid, [[(4-methylphenyl)sulfonyl]imino]-, ethyl ester(83670-53-5)

Safety Data

• Hazardous Substances Data: 83670-53-5(Hazardous Substances Data)

Upstream product

• 924-44-7 glyoxylic acid ethyl ester 
• 4083-64-1 Tosyl isocyanate 
• 4104-47-6 N-sulfinyl-p-toluenesulfonamide 
• 70-55-3 toluene-4-sulfonamide 

Downstream Products

• 64-17-5 ethanol 
• 83670-56-8 (S)-3-Methyl-2-(toluene-4-sulfonylamino)-pent-4-enoic acid ethyl ester 
• 83670-54-6 (S)-(R)-Cyclohex-2-enyl-(toluene-4-sulfonylamino)-acetic acid ethyl ester 
• 6485-63-8 ethyl 2-(4-methylphenylsulfonamido)-2-phenylacetate 
• 5465-67-8 ethyl N-tosylglycinate 

Relevant articles and documents

Imino Diels-Alder-based construction of a piperidine a-ring unit for total synthesis of the marine hepatotoxin cylindrospermopsin

The synthesis of a piperidine A-ring precursor to the alkaloid cylindrospermopsin (1) is described. The initial approach to the A-ring precursor focused on the imino Diels-Alder reaction of diene 8 with ethyl (N-tosylimino)acetate (9) to form the cycloadduct 10 as a single stereoisomer. However, all attempts to convert ester 10 to a requisite diene such as 5 were unsuccessful. An alternative strategy involved the Diels-Alder cycloaddition of N-tosylimine 9 with oxygenated diene 19 under either thermal or Lewis acid-catalyzed conditions to produce a mixture of cis and trans enones 20 and 21. Although the undesired cis-enone 20 was the major product under all reaction conditions, it could be converted to the desired trans enone 21 by acid-catalyzed isomerization. Copper-mediated conjugate addition of vinylmagnesium bromide to cis-enone 20 followed by stereoselective ketone reduction with L-Selectride produced alcohol 23, whose structure was confirmed by X-ray crystallography. Similarly, trans-enone 21 was converted to alcohol 25 whose structure and stereochemistry were also established by X-ray analysis. Alcohol 25 was then protected as the silyl ether 26, which was hydroborated at the terminal olefin to produce primary alcohol ester 28 having the stereochemistry and functionality needed for cylindrospermopsin.

Aza and oxo Diels-Alder reactions using cis-cyclohexadienediols of microbial origin: Chemoenzymatic preparation of synthetically valuable heterocyclic scaffolds

Aza and oxo Diels-Alder reactions using enantiopure cis-cyclohexadienediols were studied. These dienediols were obtained from the biotransformation of monosubstituted arenes using bacterial dioxygenases (toluene and benzoate dioxygenases). Ethyl glyoxylate and its N-tosyl imine were used as dienophiles to afford the corresponding hetero Diels-Alder bicyclic adducts with excellent regio- and stereoselectivities. Quantum chemical calculations at the B3LYP/6-31+G(d,p) level of theory were performed to rationalize the observed selectivities especially the stereochemical aspects of the cycloadditions. The synthetic importance of these adducts is highlighted for the preparation of enantiopure 2,2,3,4,5,6-hexasubstituted piperidine and tetrahydropyran from toluene.

Zinc/iron-mediated ring opening of dibromocyclopropanes for in situ Diels-Alder reactions with electron-deficient aldehydes and imines

Dibromocyclopropanes can be ring-opened by utilizing zinc dibromide in catalytic amounts and iron powder in substoichiometric amounts. The presence of the carbonyl group of aldehydes, ketones, glyoxylic esters, or imines is necessary for the ring-opening

Enantioselective intermolecular carbon-carbon bond formation of glyoxylate imines with allylstannanes catalyzed by tropos BIPHEP-gold(I) complexes with Au-Au interactions

Interactions act: The enantioselective allylation reaction of glyoxylate imines catalyzed by tropos DM-BIPHEP-gold(I) complexes with an Au-Au interaction was developed to give a higher enantioselectivity than the atropos DM-BINAP-gold complexes without an

Synthesis and reactions of sulfur-substituted indolizidinones

An aza-Diels-Alder reaction product 2 was readily converted to a tetrahydropyridine derivative 6, but its N-benzyl group was unexpectedly difficult to cleave under various conditions. On the other hand, the N-tosyl α,β-unsaturated ester 14 was transformed

A halide-initiated aza-Baylis-Hillman reaction: Generation of unnatural amino acids

A series of allenic ketones react with a glyoxylate-derived imine in the presence of MgBr2 through an aza-Morita-Baylis-Hillman (MBH) reaction. The isolation of a variety of unnatural amino acids with unique allene-containing functional groups

Br?nsted acid promoted imino-ene reactions

A series of all-carbon olefins react with glyoxylate derived imines in the presence of a phosphonic acid through an ene reaction. The isolation of the α-aminoester products is a clear indication that Br?nsted acids efficiently promote the imino-ene reacti

Palladium(II)-catalyzed one-pot enantioselective synthesis of arylglycine derivatives from ethyl glyoxylate, p-toluenesulfonyl isocyanate and arylboronic acids

A palladium(II)-catalyzed, one-pot enantioselective synthesis of arylglycine derivatives from ethyl glyoxylate, p-toluenesulfonyl isocyanate and arylboronic acids giving moderate to good yields and enantioselectivity has been developed. This reaction prov

Method for the synthesis of 4-hydroxyisoleucine and the derivatives thereof

The invention relates to a method for the synthesis of two isomers, at function OH, alone or in mixtures, of amino acids α or the derivatives thereof, having general formula (B), wherein: linkage C—O of the 4-position carbon (represented by symbol) denotes one or other of isomers III or IV, or mixtures thereof. Moreover, R1 and R2 represent: a hydrogen atom; or either R1 or R2 represents a hydrogen atom and the other substituent is a radical Ra, an acyl group —CORa, such as acetyl, or a functional group —COORa, —SO2Ra, —N (Ra, Rb), Ra and Rb, which are identical or different, representing a C1-C12 linear or branched alkyl radical, optionally substituted, an aryl group with one or more aromatic rings and heterocycles, comprising between 5 and 8C, optionally substituted, or aralkyl, the alkyl substituent and the aryl group being as defined above; or R1 and R2 both represent a substituent as defined above. R3 represents a hydrogen atom or Ra and R4 has the significance of Ra. The invention is characterised in that it comprises: the isomerisation of a compound having formula (I), wherein R1, R2, Ra, R3 and R4 are as defined above, such as to produce a compound having formula (II); and the reduction of the carbonyl function thereof which, depending on the catalytic system employed and the formula (I) compound used, produces one of the isomers having general formula (III) or (IV) or a mixture thereof having formula (B). The invention can be used for the synthesis of (2S, 3R, 4S)-4-hydroxyisoleucine.

Asymmetric multicomponent reactions: Diastereoselective synthesis of substituted pyrrolidines and prolines

A novel diastereoselective synthesis of substituted pyrrolidines has been developed. Asymmetric multicomponent reactions of optically active phenyldihydrofuran, N-tosyl imino ester, and silane reagents in a one-pot operation afforded highly substituted py