139243-55-3

Usage

Uses

Used in Pharmaceutical Industry:
Butanoic acid, 3-amino-, methyl ester, hydrochloride, (3S)is used as an intermediate in the synthesis of various pharmaceutical compounds for its unique structural features and reactivity. The specific (3S)configuration may provide advantages in the development of enantiomerically pure drugs, which can be crucial for the desired biological activity and reduced side effects.
Used in Agricultural Industry:
In agriculture, Butanoic acid, 3-amino-, methyl ester, hydrochloride, (3S)may be utilized as a precursor for the development of agrochemicals, such as pesticides or plant growth regulators. Its unique structure could contribute to the creation of novel and effective products that can enhance crop protection or yield.
Used in Chemical Synthesis:
Butanoic acid, 3-amino-, methyl ester, hydrochloride, (3S)is used as a building block in the synthesis of specialty chemicals, taking advantage of its reactive functional groups and the specific stereochemistry provided by the (3S)configuration. This can lead to the production of innovative materials with tailored properties for various applications.

Upstream product

• 75-77-4 chloro-trimethyl-silane 
• 3775-72-2 L-3-aminobutyric acid 
• 67-56-1 methanol 
• 106539-14-4 (S)-methyl 3-(tert-butyloxycarbonylamino)butyrate 
• 113034-32-5 methyl ester of (S)-3-(benzoylamino)butanoic acid 
• 158851-30-0 (S)-3-tert-butoxycarbonylaminobutyric acid 
• 137132-12-8 (3RS)-3-aminobutanoic acid methyl ester hydrochloride 
• 108-59-8 malonic acid dimethyl ester 

Downstream Products

• 1219839-41-4 C₁₂H₂₁NO₅ 
• 147034-51-3 (S)-3-Amino-N-methyl-butyramide 

Relevant academic research and scientific papers

Stabilization of β-peptide helices by direct attachment of trifluoromethyl groups to peptide backbones

The 14-helix structure of oligo-β-peptides was significantly stabilized by direct attachment of CF3 groups to their backbones. Our studies indicate that this stabilization originates from the CF 3-promoted increase in the intramolecular hydrogen-bonding ability of their backbone amides, leading to a novel strategy to stabilize peptide folding.

Reverse Turn Foldamers: An Expanded β-Turn Motif Reinforced by Double Hydrogen Bonds

Hybrid tetrapeptides sharing a backbone with a central α/β-dipeptide segment flanked by aromatic ?3-amino acid residues fold into the same hairpin conformation with an expanded β-turn. This hairpin/β-turn motif is general for accommodating different α- A nd β-amino acid residues. Replacing glycine with other α-amino acid residues has an insignificant influence on or slightly decreases the stabilities of the folded conformations; substituting β-alanine with other β-amino acid residues enhances the stabilities of the folded structures.

An extension of the 'Bip method': Induced axial chirality in a series of dipeptides based on Bip/β2,2-HBip combined with Ala/β3-HAla

In the search for an extension of the 'Bip method' for determining the absolute configuration of β-amino acids and β-peptides, dipeptides based on β2,2-HBip/l(d)-Ala, Bip/l-β3-HAla, and β2,2-HBip/l-β3-HAla were synthesized in solution and the induced circular dichroism (ICD) in their biphenyl core evaluated in comparison with the previously investigated Bip/l(d)-Ala series. Weak, poorly informative ICDs were observed in MeOH solution for the linear N-Boc protected dipeptide methyl esters based on β2,2-HBip, as well as for those with Ala/β3-HAla at the N-terminus of Bip/β2,2- HBip. However, a significant ICD was recorded for Boc-Bip-l-β3- HAla-OMe. These results were confirmed by low-temperature 1H NMR spectroscopy studies of the dipeptides in CDCl3 and CD3OD solutions, showing two diastereoisomeric conformers in significantly different populations for Boc-Bip-l-β3-HAla-OMe in CD3OD. In general, ICDs were found to be weaker for dipeptides containing β-amino acids as compared to those of their α-amino acid counterparts.

Indoloazepinone-Constrained Oligomers as Cell-Penetrating and Blood–Brain-Barrier-Permeating Compounds

Non-cationic and amphipathic indoloazepinone-constrained (Aia) oligomers have been synthesized as new vectors for intracellular delivery. The conformational preferences of the [l-Aia-Xxx]n oligomers were investigated by circular dichroism (CD) and NMR spectroscopy. Whereas Boc-[l-Aia-Gly]2,4-OBn oligomers 12 and 13 and Boc-[l-Aia-β3-h-l-Ala]2,4-OBn oligomers 16 and 17 were totally or partially disordered, Boc-[l-Aia-l-Ala]2-OBn (14) induced a typical turn stabilized by C5- and C7-membered H-bond pseudo-cycles and aromatic interactions. Boc-[l-Aia-l-Ala]4-OBn (15) exhibited a unique structure with remarkable T-shaped π-stacking interactions involving the indole rings of the four l-Aia residues forming a dense hydrophobic cluster. All of the proposed FITC-6-Ahx-[l-Aia-Xxx]4-NH2 oligomers 19–23, with the exception of FITC-6-Ahx-[l-Aia-Gly]4-NH2 (18), were internalized by MDA-MB-231 cells with higher efficiency than the positive references penetratin and Arg8. In parallel, the compounds of this series were successfully explored in an in vitro blood–brain barrier (BBB) permeation assay. Although no passive diffusion permeability was observed for any of the tested Ac-[l-Aia-Xxx]4-NH2 oligomers in the PAMPA model, Ac-[l-Aia-l-Arg]4-NH2 (26) showed significant permeation in the in vitro cell-based human model of the BBB, suggesting an active mechanism of cell penetration.

Aryl imidazole derivative and application thereof

The invention relates to an aryl imidazole derivative and application thereof. The aryl imidazole derivative is a compound shown as a formula (I) in the description or pharmaceutically acceptable salt thereof. The invention also discloses application of the aryl imidazole derivative in preparation of drugs for treating cancers. The invention further discloses application of the aryl imidazole derivative in preparation of drugs for treating diseases caused by EGFR mutation.

A 3 (R) / (S)-amino-1-butanol method for the preparation of

The invention provides a method for preparing 3(R)/(S)-amidogen-1-butanol. The method comprises the steps that firstly, benzamide reacts with acetoacetic ester under the catalyzing action of p-toluenesulfonic acid, so that 3-benzamido-2-butene acid ester is generated; secondly, catalytic hydrogenation is conducted by using a chiral rhodium-diphosphine ligand compound as a catalyst for enantioselective hydrogenation, so that 3(R)/(S)-benzamide butyrate is generated highly selectively; thirdly, benzoyl is removed by means of mixed solvent of concentrated hydrochloric acid and alcohol, so that 3(R)/(S)-amino-crotonic acid ester hydrochloride is generated; finally, optically pure 3(R)/(S)-amidogen-1-butanol is obtained after ester carbonyl is reduced by means of hydronoron. According to the method, the raw materials are low in cost and easy to obtain, the technological operation is easy and convenient, resolution is not needed, the yield is high, cost is low, environmental friendliness is achieved, the optical purity of product is high, and the method is more suitable for industrial production.

Synthesis of chiral non-racemic intermediates and Arg-Gly-Asp mimetics by CaLB-catalyzed resolution

The reactivity of both the ester and amine functions present in β-amino esters was tested in order to obtain the synthesis of enantiopure αvβ3 and α5β1 integrin ligands. CaLB successfully catalyzed both the enantioselective transesterification and the N-acylation of racemic β-amino esters, allowing the isolation of intermediates for the preparation of Arg-Gly-Asp (RGD) mimetic compounds. In particular, a CaLB-catalyzed amidation reaction with unprotected p-aminobenzylamine reduced the number of synthetic steps, thus avoiding protection and deprotection of the intermediate compounds. Following this procedure, RGD mimetics were isolated with high yields and enantiomeric purities.

The Bip method, based on the induced circular dichroism of a flexible biphenyl probe in terminally protected -Bip-Xaa*-dipeptides, for assignment of the absolute configuration of β-amino acids

An induced axial chirality of the biphenyl core of the Bip (2′,1′:1,2;1″,2″:3,4-dibenzcyclohepta-1, 3-diene-6-amino-6-carboxylic acid) residue in the terminally protected dipeptides Boc-Bip-β-Xaa*-OMe (β-Xaa* = L-β3-HAla, L-β3-HVal,

Enantioselective Synthesis of β-Amino Acids. 2. Preparation of the like Stereoisomers of 2-Methyl- and 2-Benzyl-3-aminobutanoic Acid

An improved procedure for the preparation of (R)- and (S)-3-aminobutanoic acids (2a) through diastereomer separation of the corresponding (1'S)-N-phenethyl derivatives 1 is reported.From 2a, the four possible stereoisomeric perhydropyrimidin-4-ones 4 were prepared through the amide 2c and the Schiff base 3.In the cyclization of 3, the cis products 4 predominate ca. 95:5.These heterocycles can be alkylated (LDA, RX), as demonstrated by methylation and benzylation, with formation of a single diastereoisomer (5, 6).Hydrolysis (6 N aqueous HCl) of these 5,6-dialkylperhydropyrimidin-4-ones leads to the free amino acids 7-10.