4052-59-9

Usage

Purification Methods

Recrystallise 2-(2-thienyl)glycine by dissolving it in H2O (1g in 3 mL), adjusting the pH to 5.5 with aqueous NH3, diluting with MeOH (20 mL), stirring, adjusting the pH to 5.5 and cooling to 0o. Also recrystallise it from small volumes of H2O. [R-isomer: Nishimura et al. Nippon Kagaku Zasshi 82 1688 1961, S-isomer: Johnson & Panetta Chem Abstr 63 14869 1965, Johnson & Hardcastle Chem Abstr 66 10930 1967, RS-isomer: LiBassi et al. Gazz Chim Ital 107 253 1977.] The (±) N-acetyl derivative has m 191o (from H2O) [Schouteenten et al. Bull Soc Chim Fr II 248, II 252 1978].

InChI:InChI=1/C6H7NO2S/c8-6(9)4-7-5-2-1-3-10-5/h1-3,7H,4H2,(H,8,9)

Upstream product

• 98-03-3 thiophene-2-carbaldehyde 
• 4075-59-6 2-thiopheneglyoxylic acid 
• 26878-13-7 methyl 2-thienylglyoxylate 
• 126402-94-6 2,2-Dimethyl-propionic acid (2S,3S,4R,5R)-2-[((R)-tert-butylcarbamoyl-thiophen-2-yl-methyl)-formyl-amino]-4,5-bis-(2,2-dimethyl-propionyloxy)-tetrahydro-pyran-3-yl ester 
• 21124-40-3 D,L-(2-thienyl)glycine 
• 1355742-75-4 (S)-2-benzyloxycarbonylamino-2-(thiophen-2-yl)-acetonitrile 
• 65700-48-3 N-carbamyl-D-(-)2-thienylglycine 
• 145057-99-4 (S)-2-<(R)-2-hydroxy-1-phenylethylamino>-2-(2-thienyl)ethanoic acid 
• 145058-07-7 methyl (S)-2-<(R)-2-hydroxy-1-phenylethylamino>-2-(2-thienyl)ethanoate 
• 110728-00-2 C₁₄H₁₃NO₃S 
• 97101-15-0 (2R)-(-)-2-<(1S,2S)-(2-Hydroxy-1-hydroxymethyl-2-phenylethyl)amino>-2-(2-thienyl)essigsaeure 
• 97036-29-8 (2S)-(-)-2-<(1S,2S)-(2-Hydroxy-1-hydroxymethyl-2-phenylethyl)amino>-2-(2-thienyl)essigsaeure 
• 1027925-78-5 2-tert-butoxycarbonylamino-2-thiophen-2-yl-malonic acid diethyl ester 
• 408346-66-7 diethyl 2-amino-2-(2-thienyl)-malonate 

Downstream Products

• 112395-52-5 N-<(o-nitrophenyl)sulfenyl>-D,L-2-thienylglycine 
• 171661-56-6 2-amino-2-(thiophen-2-yl)ethan-1-ol 
• 112395-54-7 N-<(o-nitrophenyl)sulfenyl>-D,L-2-thienylglycine (+)-β-fenchyl ester 
• 891789-93-8 C₁₃H₁₁ClN₂O₃S 
• 891789-96-1 C₂₀H₁₅ClN₄O₂S 
• 162927-66-4 4-(2-thienyl)-2-(trifluoromethyl)-3-oxazolin-5-one 
• 122460-66-6 4-(p-chlorophenyl)-2-(trifluoromethyl)-1,3-oxazol-5-one 
• 14675-98-0 N-Boc-amino(2-thienyl)acetic acid 
• 59966-06-2 L-α-[[[(4-methoxyphenyl)-methoxy]carbonyl]amino]-2-thiopheneacetic acid 
• 1035868-78-0 C₁₅H₁₁NO₂S₂ 
• 416879-89-5 (Ph3P)PdCl(η(2)-N,O-NH2CH(2-thienyl)COO) 
• 4052-59-9 (R)-amino(thiophen-2-yl)acetic acid 
• 4052-59-9 (2S)-amino(2-thienyl)acetic acid 
• 1469538-27-9 2-phenyl-5-(thiophen-2-yl)pyrazolo[1,5-c]quinazoline 

Relevant academic research and scientific papers

Reductive amination of ketonic compounds catalyzed by Cp*Ir(III) complexes bearing a picolinamidato ligand

Cp*Ir complexes bearing a 2-picolinamide moiety serve as effective catalysts for the direct reductive amination of ketonic compounds to give primary amines under transfer hydrogenation conditions using ammonium formate as both the nitrogen and hydrogen source. The clean and operationally simple transformation proceeds with a substrate to catalyst molar ratio (S/C) of up to 20,000 at relatively low temperature and exhibits excellent chemoselectivity toward primary amines.

CATALYST COMPOUNDS

The present invention relates to an iridium-based catalyst compound for hydrogenating reducible moieties, especially imines and iminiums, the catalyst compounds being defined by the formulas: where ring B is either itself polycyclic, or ring B together with R is polycyclic. The catalysts of the invention are particularly effective in reductive amination procedures 10 which involve the in situ generation of the imine or iminium under reductive hydrogenative conditions.

Primary amines by transfer hydrogenative reductive amination of ketones by using cyclometalated IrIII catalysts

Cyclometalated iridium complexes are found to be versatile catalysts for the direct reductive amination (DRA) of carbonyls to give primary amines under transfer-hydrogenation conditions with ammonium formate as both the nitrogen and hydrogen source. These complexes are easy to synthesise and their ligands can be easily tuned. The activity and chemoselectivity of the catalyst towards primary amines is excellent, with a substrate to catalyst ratio (S/C) of 1000 being feasible. Both aromatic and aliphatic primary amines were obtained in high yields. Moreover, a first example of homogeneously catalysed transfer-hydrogenative DRA has been realised for β-keto ethers, leading to the corresponding β-amino ethers. In addition, non-natural α-amino acids could also be obtained in excellent yields with this method. Reduce the work! A broad range of ketones have been successfully aminated to afford primary amines under transfer-hydrogenation conditions by using ammonium formate as the amine source and 0.1 mol % of a cyclometalated IrIII catalyst (see scheme). Copyright

CATALYST COMPOUNDS

The present invention relates to an iridium-based catalyst compound for hydrogenating reducible moieties, especially imines and iminiums, the catalyst compounds being defined by the formulas: where ring B is either itself polycyclic, or ring B together with R is polycyclic. The catalysts of the invention are particularly effective in reductive amination procedures 10 which involve the in situ generation of the imine or iminium under reductive hydrogenative conditions.

Enantioselective hydrocyanation of N-protected aldimines

Enantioselective hydrocyanation of N-benzyloxycarbonyl aldimines catalyzed by a Ru[(S)-phgly]2[(S)-binap]/C6H5OLi system or a bimetallic complex [Li{Ru[(S)-phgly]2[(S)-binap]}]Cl affords the amino nitriles in 92 - 99% ee. The reaction is carried out in tert-C 4H9OCH3 with a substrate-to-catalyst molar ratio in the range of 500 - 5000 at -20 to 0°C. Primary, secondary, and tertiary alkyl imines as well as the aryl and heteroaryl substrates are smoothly cyanated to produce the desired products in high yield.

COMPOSITIONS AND METHODS FOR CYCLOFRUCTANS AS SEPARATION AGENTS

The present invention relates to derivatized cyclofructan compounds, compositions comprising derivatized cyclofructan compounds, and methods of using compositions comprising derivatized cyclofructan compounds for chromatographic separations of chemical species, including enantiomers. Said compositions may comprise a solid support and/or polymers comprising derivatized cyclofructan compounds.

One-pot, regioselective synthesis of substituted arylglycines for kinetic resolution by penicillin G acylase

Amido-alkylation of electron-rich arenes with phenylacetamide and glyoxylic acid offers an in-expensive route to a large variety of N-phenylacetylated arylglycines that are suited for immediate enzymatic resolution by penicillin G acylase. When performed under mild conditions at 5 °C in acetic acid/HCl, this simple one-pot operation resulted in the formation of single regioisomers only (≥98%). Subsequent kinetic resolution of the amino acid derivatives by penicillin G acylase at pH 8.0 occurred generally with E values >100 and thus furnished free (S)-configurated arylglycines with high enantiomeric purity. The corresponding enantiopure (R)-substrates, easily separable by a phase-selective extraction process, provided the corresponding (R)-enantiomers upon conventional hydrolysis. This one-pot, two-step procedure for arylglycine synthesis, resolution and work-up requires a minimum of equipment and grants rapid access to both enantiopure (S)- and (R)-antipodes of non-natural α-amino acids in small-to large-scale quantities.

Catalytic Leuckart-Wallach-type reductive amination of ketones

A Cp*Rh(III) complex catalyzes reductive amination of ketones using HCOONH4 at 50-70°C to give the corresponding primary amines in high yields. The reaction is clean and operationally simple and proceeds at a lower temperature and with higher chemoselectivity than the original Leuckart-Wallach reaction. The new method has been applied to the synthesis of α-amino acids directly from α-keto acids.

Synthesis of arylglycines by reaction of diethyl N-Boc-iminomalonate with organomagnesium reagents

Diethyl N-Boc-iminomalonate (3), prepared on multigram scale, served as a stable and highly reactive electrophilic glycine equivalent which reacted with organomagnesium compounds affording substituted aryl N-Boc-aminomalonates. Subsequent hydrolysis produced arylglycines.

Peptides with an insulin-like action

Peptides with an insulin-like action, of formula I: STR1 in which G is a hydrogen atom, an amino add residue, or a monosubstituted or polysubstituted amino acid; D is an amino acid residue, a phosphoamino acid residue, a monosaccharide residue, or a covalent bond; E is --NH--(CH2)n --NR52, a glycerol residue, or --NH--(CH2)p --R6 --R7 ; R1 is (C1 -C4)-alkyl or =O; R2 is a sulfhydryl protecting group, (C1 -C3)-alkyl, or a hydrogen atom; R3 and R4, independently of one another, are a hydrogen atom or methyl; R5, each being identical or different, is a hydrogen atom, 1 to 6 monosaccharide residues, or 1 to 6 monosubstituted or polysubstituted monosaccharide residues; R6 is O PO4 H, PO2 H, NHCOO, S or OCOO; R7 is a hydrogen atom, 1 to 6 monosaccharide residues, or 1 to 6 monosubstituted or polysubstituted monosaccharide residues; w is an integer 1 or 2; their preparation and use for treatment of diabetes mellitus or insulin-independent diabetes.