595-40-4

Usage

Purification Methods

Crystallise it from aqueous Me2CO, or better by dissolving in H2O and adding excess Me2CO. [Baker et al. J Am Chem Soc 74 4701 1952, Greenstein & Winitz The Chemistry of the Amino Acids J. Wiley, Vol 3 p 2573-2577 1961.]

InChI:InChI=1/C5H11NO2/c1-3-5(2,6)4(7)8/h3,6H2,1-2H3,(H,7,8)/t5-/m0/s1

Upstream product

• 29588-10-1 (+/-)-2-formylamino-2-methyl-butyric acid 
• 58279-59-7 N-chloroacetyl-DL-isovaline 
• 29588-12-3 N-formyl-L-isovaline 
• 59209-90-4 (RS)-2-amino-2-methylbutanamide 
• 123463-88-7 (1R,3R,4S)-8-phenyl-p-menthan-3-yl (2'S)-2'-amino-2'-methylbutanoate 
• 295799-94-9 (3S,6R)-N-1-(tert-butoxycarbonyl)-3-ethyl-6-isopropyl-3-methyl-5-phenyl-1,2,3,6-tetrahydro-2-pyrazinone 
• 123463-75-2 (1R,3R,4S)-8-phenyl-p-menthan-3-yl hydrogen ethyl(methyl)malonate 
• 595-39-1 DL-isovaline 
• 1204593-74-7 (3S,6S)-1,4-N,N-[(S)-phenylethyl]-3,6-diethyl-3,6-dimethylpiperazine-2,5-dione 
• 13893-46-4 ethyl (R)-2-amino-2-methylbutyrate 
• 4475-95-0 2-amino-2-methylbutanenitrile 
• 1266681-11-1 (3S,5aR,6aS,7aS)-3-ethyl-5,5a,6,6a,7,7a-hexahydro-3,6,6,7a-tetramethylbicyclo[4.1.0]hept-1⁽⁶⁾eno[3,4-b][1,4]oxazin-2(3H)-one 

Downstream Products

• 13893-46-4 ethyl (R)-2-amino-2-methylbutyrate 
• 151171-11-8 (S)-2-((tert-butoxycarbonyl)amino)-2-methylbutanoic acid 
• 3739-30-8 2-hydroxy-2-methylbutyric acid 
• 92760-72-0 L-isovalin methyl ester hydrochloride 
• 265312-79-6 N^α-Z-L-Iva-OH 
• 857478-30-9 N-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-isovaline 
• 160171-18-6 (+)-S-zoxamide 
• 208262-74-2 C₁₃H₁₆FNO₃ 
• 1177452-06-0 Z-L-Iva-Aib-OtBu 
• 1177452-09-3 Z-L-Leu-L-Iva-Aib-OtBu 

Relevant academic research and scientific papers

Amino Acid-Derived trans-N-Chloroformylimidazolidinones: Scalable, Stereoselective Synthesis, Structure, and Utility

N-acyl imidazolidinones, which are key intermediates in the stereoselective synthesis of amino acids by "self-regeneration of stereochemistry" methods, are classically made by only moderately diastereoselective methods. We now report that cyclization of pivaldimino-amides with phosgene in the presence of pyridine may be made fully diastereoselective for the trans-N-chloroformylimidazolidinones, and we detail the conformational features of the products. We show that despite the presence of the electrophilic carbamoyl chloride function the products show remarkable stability and may be deprotonated to form enolates with useful reactivity for the synthesis of amino acid derivatives.

High-chirality method for selectively synthesizing alpha-disubstituted alpha-amino acid

The invention discloses a high-chirality method for selectively synthesizing alpha-disubstituted alpha-amino acid. The high-chirality method for selectively synthesizing alpha-disubstituted alpha-amino acid is characterized by comprising the following steps: step one, reacting S-tert-butanesulfinyl amide or R-tert-butanesulfinyl amide, R-beta substituted ethyl pyruvate and tetraethyl titanate in atetrahydrofuran solvent to obtain a compound C; step two, reacting the compound C with alkyl substituted magnesium bromide under the catalyzing effect of zinc dimethyl in tetrahydrofuran to obtain acompound E; step three, reacting the compound E under the effect of ammonium chloride and anhydrous hydrogen chloride to obtain a compound F; and step four, hydrolyzing the compound F in an ethanol aqueous solution of sodium hydroxide to obtain hydrochloride of a compound G, and carrying out ion exchange to obtain the compound G. The chiral selective reaction is greatly improved, and the method issimple in process, uses cheap and easily obtained raw materials, is simple and convenient to operate, is quite suitable for industrial mass production, and has quite extensive industrial applicationprospect and market value.

Synthesis and conformational analysis of efrapeptins

The efrapeptin family of peptide antibiotics produced by the fungus Tolypocladium niveum, and the neo-efrapeptins from the fungus Geotrichum candidumare inhibitors of F1-ATPase with promising antitumor, antimalaria, and insecticidal activity. They are rich in Cα- dialkyl amino acids (Aib, Iva, Acc) and contain one β-alanine and several pipecolic acid residues. The C-terminus bears an unusual heterocyclic cationic cap. The efrapeptins C-G and three analogues of efrapeptin C were synthesized using α-azido carboxylic acids as masked amino acid derivatives. All compounds display inhibitory activity toward F1-ATPase. The conformation in solution of the peptides was investigated with electronic CD spectroscopy, FT-IR spectroscopy, and VCD spectroscopy. All efrapeptins and most efrapeptin analogues were shown to adopt helical conformations in solution. In the case of efrapeptin C, VCD spectra proved that a 310-helix prevails. In addition, efrapeptin C was conformationally studied in detail with NMR and molecular modeling. Besides NOE distance restraints, residual dipolar couplings (RDC) observed upon partial alignment with stretched PDMS gels were used for the conformational analysis and confirmed the 310-helical conformation. Copyright

Asymmetric synthesis of α-methyl-α-amino acids via diastereoselective alkylation of (1s)-(+)-3-carene derived tricyclic iminolactone

A novel carene-based alanine-equivalent tricyclic iminolactone 16 has been synthesized via stereoselective dihydroxylation of the double bond, IBX oxidation of the secondary alcohol, esterification of the tertiary alcohol, deprotection of the resulting ester, and subsequent cyclization from commercially available (1S)-(+)-3-carene in 79% overall yield. The iminolactone 16 demonstrated high reactivity toward alkylation with a wide range of electrophiles at room temperature under phasetransfer catalysis conditions. The alkylated products were produced with excellent diastereoselectivities (>98% de) in good isolated yields (86-94%). High yields (83-91%) of optically pure (S)-R-methyl-R-substituted-R-amino acids were obtained by basic hydrolysis of the dialkylated iminolactones with the recovery of the chiral auxiliary 15 (78-87%).

(S)-α-methyl,α-amino acids: A new stereocontrolled synthesis

A new and convenient stereocontrolled synthesis of the optically pure (S)-α-methyl,α-amino acids 6(a-d) that exploits the chiral synthon 1,4-N,N-[(S)-1-phenylethyl]-piperazine-2,5-dione (1) is described. The (S)-1-phenylethyl group, bonded to each of the N-atoms of the 2,5-diketopiperazine, acts as a chiral inductor in the first alkylation, while the steric hindrance appears to be the determining factor of stereocontrol in third and forth alkylation.

Halo-substituted (S)-N-(2-benzoylphenyl)-1-benzylpyrolidine-2-carboxamides as new chiral auxiliaries for the asymmetric synthesis of (S)-α-amino acids

The synthesis of new chiral auxiliaries (S)-N-(2-benzoylphenyl)-1-(3,4-dichlorobenzyl)-pyrrolidine-2-carboxamide (1a), (S)-N-(2-benzoylphenyl)-1-(pentafluorobenzyl)pyrrolidine-2-carboxamide (1b), and (S)-N-(2-benzoylphenyl)-1-(4-isopropoxytetrafluorobenzyl) pyrrolidine-2-carboxamide (1c) and their application in the asymmetric synthesis of amino acids using NiII complexes of their Schiff's bases with alanine and glycine are described. Compound la is particularly appropriate for highly stereoselective synthesis of α-methyl-α -amino acids with high enatiomeric purity (ee >95%).

Synthesis of isotope-labeled aminoacids contained in servamycin antibiotic

Approach was developed to a preparative synthesis of isotope-labeled aminoacids contained in servamycin IIB antibiotic. Glutamines labeled with 15N, 13C, and 2H were prepared in 70-80% yield starting with the corresponding labeled glutamic acids under catalysis with the glutamine synthetase enzyme. 15N-2-aminoisohutanoic acid and 15N-isovaline were obtained by Strecker method in 65 and 31% yields respectively. All compounds synthesized were identified and characterized by NMR spectroscopy.

Chiral salen-metal complexes as novel catalysts for the asymmetric synthesis of α-amino acids under phase transfer catalysis conditions

Chiral salen-metal complexes have been tested as catalysts for the C-alkylation of Schiff's bases of alanine and glycine esters with alkyl bromides under phase-transfer conditions (solid sodium hydroxide, toluene, ambient temperature, 1-10 mol% of the catalyst). The best catalyst, which was derived from a Cu(II) complex of (1R, 2R or 1S,2S)-[N,N′-bis(2′-hydroxybenzylidene)]-1,2-diaminocyclohexane, gave α-amino and α-methyl-α-amino acids with enantiomeric excesses of 70-96%.

Applications of the sulfinimine-mediated asymmetric strecker synthesis to the synthesis of α-alkyl α-amino acids

Addition of Et2AlCN and i-PrOH to ketosulfinimines (N-sulfinyl imines) affords corresponding α-alkyl α-amino nitriles in moderate to good yields. The diastereoselectivity is largely dependent on the E/Z isomer ratio of the ketosulfinimine. Hydrolysis of the diastereomerically pure amino nitriles affords enantiopure α-alkyl α-amino acids in moderate to good yields.

Asymmetric synthesis of α-Methyl α-Amino Acids through diastereoselective alkylation under mild reaction conditions of an iminic alanine template with a 1,2,3,6-Tetrahydro-2-Pyrazinone structure

(6R)-6-Isopropyl-3-methyl-5-phenyl-1,2,3,6-tetrahydro-2-pyrazinone, obtained from (R)-valine and (S)-alanine, is highly diastereoselectively alkylated at room temperature by: a) activated alkyl halides under solid-liquid PTC conditions, b) non-activated alkyl halides with organic bases, c) electrophilic olefins employing both solid-liquid PTC conditions and organic bases, and d) allylic carbonates by means of palladium catalysis under neutral conditions. Enantiomerically pure (S)-α-methyl α-amino acids 8 are obtained by hydrolysis of the alkylated pyrazinones.