15399-22-1

Basic information

• Product Name: H-ABU-OME HCL
• Synonyms: H-ABU-OME HCL;H-Abu-OMe;(S)-Methyl 2-aminobutanoate;ethyl (S)-2-aminobutanoate hydrochlori;Levetiracetam Impurity J
• CAS NO: 15399-22-1
• Molecular Formula: C₅H₁₁NO₂
• Molecular Weight: 153.608
• Mol File: 15399-22-1.mol

Chemical Properties

• Boiling Point: 127.8±13.0 °C(Predicted)
• Appearance: /
• Density: 0.987±0.06 g/cm3(Predicted)
• Storage Temp.: under inert gas (nitrogen or Argon) at 2–8 °C
• PKA: 7.89±0.29(Predicted)
• CAS DataBase Reference: H-ABU-OME HCL(CAS DataBase Reference)
• NIST Chemistry Reference: H-ABU-OME HCL(15399-22-1)
• EPA Substance Registry System: H-ABU-OME HCL(15399-22-1)

Safety Data

• Hazardous Substances Data: 15399-22-1(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
H-ABU-OME HCL is used as a key intermediate in the synthesis of methylsulphonamide-based small molecule legumain inhibitors. These inhibitors are essential in the development of potential therapeutic agents for various diseases and conditions, as they target specific enzymes involved in these pathological processes.
In the synthesis of these inhibitors, H-ABU-OME HCL serves as a building block, providing the necessary structure and functional groups required for the formation of the final product. Its use in this application is driven by its reactivity and compatibility with other molecules involved in the synthesis process, making it a valuable component in the development of novel pharmaceuticals.

Upstream product

• 67-56-1 methanol 
• 34306-42-8 Boc-Abu 
• 7324-11-0 (S)-2-amino-butanamide 
• 75266-39-6 methyl (S)-2-<<(benzyloxy)carbonyl>amino>-4-(methylsulfinyl)butanoate 
• 2491-18-1 (S)-methyl 2-amino-4-(methylthio)butanoate hydrochloride 
• 56762-93-7 methyl (S)-2-(benzyloxycarbonylamino)-4-methylmercaptobutanoate 
• 407578-43-2 (3S,6S)-3-isopropyl-6-ethylpiperazine-2,5-dione 
• 186581-53-3 diazomethane 
• 1492-24-6 L-2-aminobutyric acid 
• 75266-40-9 N-benzyloxycarbonyl-L-α-vinylglycine methyl ester 

Downstream Products

• 7652-88-2 α-Z-N^ε-BOC-L-Lysyl>-L-α-amino-buttersaeure-methylester 
• 164453-64-9 (3S,6S)-3,6-diethylpiperazine-2,5-dione 
• 53726-14-0 (S)-2-amino-butanamide hydrochloride 
• 7324-11-0 (S)-2-amino-butanamide 
• 5959-29-5 S-(+)-2-amino-n-butyric acid hydrochloride 

Relevant articles and documents

Preparation and biological evaluation of soluble tetrapeptide epoxyketone proteasome inhibitors

A series of novel tetrapeptidyl epoxyketone inhibitors of 20S proteasome was designed and synthesized. To fully understand the SAR, various groups at R1, R2, R3, R4 and R5 positions, including aromatic and aliphatic substituents were designed, synthesized and biologically assayed. Based on the enzymatic results, seven compounds were selected to evaluate their cellular activities and soluble compound 36 showed strong potency against human multiple myeloma (MM) cell lines. Microsomal stability results indicated that compound 36 was more stable in mice, rat and human microsomes than marketed carfilzomib. The in vivo activities of this compound were evaluated with the xenograft mice models of MM cell lines ARH77 and RPMI-8226 with luciferase expression and the T/C value of the two models were 49.5% and 37.6%, respectively. To evaluate the potential cardiovascular toxicity, inhibition of hERG ion channel in HEK293 cells by compound 36 and carfilzomib was carried out. The results indicated that 36 had no binding affinity for the hERG ion channel while carfilzomib could bind it with IC50 of 92.1 μM.

Continuous-flow protocol for the synthesis of enantiomerically pure intermediates of anti epilepsy and anti tuberculosis active pharmaceutical ingredients

Continuous-flow production of chiral intermediates plays an important role in the development of building blocks for Active Pharmaceutical Ingredients (APIs), being α-amino acids and their derivatives widely applied as building blocks. In this work we developed two different strategies for the synthesis of intermediates used on the synthesis of levetiracetam/brivaracetam and ethambutol. The results obtained show that methionine methyl ester can be continuously converted to the desired ethambutol intermediate by RANEY Nickel dessulfurization/reduction strategy whereas levetiracetam/brivaracetam intermediates could be synthesized by both RANEY Nickel (without H2) and Pd/C-H2 approach or by photochemical desulfurization.

Structure-Guided Design and Development of Potent and Selective Dual Bromodomain 4 (BRD4)/Polo-like Kinase 1 (PLK1) Inhibitors

The simultaneous inhibition of polo-like kinase 1 (PLK1) and BRD4 bromodomain by a single molecule could lead to the development of an effective therapeutic strategy for a variety of diseases in which PLK1 and BRD4 are implicated. Compound 23 has been found to be a potent dual kinase-bromodomain inhibitor (BRD4-BD1 IC50 = 28 nM, PLK1 IC50 = 40 nM). Compound 6 was found to be the most selective PLK1 inhibitor over BRD4 in our series (BRD4-BD1 IC50 = 2579 nM, PLK1 IC50 = 9.9 nM). Molecular docking studies with 23 and BRD4-BD1/PLK1 as well as with 6 corroborate the biochemical assay results.

BET (bromodomain and extraterminal domain)/HDAC (histone deacetylase) double-target inhibitor, and preparation method and application thereof

The invention discloses a BET (bromodomain and extraterminal domain)/HDAC (histone deacetylase) double-target inhibitor, and a preparation method and application thereof. The structure of the double-target inhibitor is as shown in the specification, wherein n=2-6. Compared with the prior art, the double-target inhibitor has the advantage that pharmacophore of a BET inhibitor BI-2536 and pharmacophore of an HDAC inhibitor are spliced by a Linker to obtain a novel BET/HDAC inhibitor with BET/HDAC double-target inhibition effect. The preparation method is simple, mild in condition and easy to implement.

DIHYDROPTERIDINONE DERIVATIVES, PREPARATION PROCESS AND PHARMACEUTICAL USE THEREOF

Dihydroperidinone derivatives, preparation process and pharmaceutical use thereof are disclosed. Specially, new dihydroperidinone derivatives represented by general formula (I), wherein each substituent of the general formula (I) is defined as in the description, their preparation process, pharmaceutical compositions comprising said derivatives and their use as therapeutical agents, especially as Plk kinase inhibitors are disclosed.

DIHYDROPTERIDINONE DERIVATIVES, PREPARATION PROCESS AND PHARMACEUTICAL USE THEREOF

Dihydroperidinone derivatives, preparation process and pharmaceutical use thereof are disclosed. Specially, new dihydroperidinone derivatives represented by general formula (I), wherein each substituent of the general formula (I) is defined as in the description, their preparation process, pharmaceutical compositions comprising said derivatives and their use as therapeutical agents, especially as Plk kinase inhibitors are disclosed.

QUINAZOLINEDIONE CHYMASE INHIBITORS

Disclosed are small molecule inhibitors which are useful in treating various diseases and conditions involving Chymase.

PROCESSES FOR THE PREPARATION OF LEVETIRACETAM, ITS INTERMEDIATE AND THE USE OF LEVETIRACETAM IN PHARMACEUTICAL COMPOSITIONS

The invention relates to processes for the preparation of (S)-2-aminobutanamide of Formula I, and to the use of the compound of Formula I as intermediate for the preparation of levetiracetam of Formula (II).The invention also relates to a process for the preparation of levetiracetam and pharmaceutical compositions that include the levetiracetam.

Conjugate additions of organocuprates to a 3-methylene-6-isopropyldiketopiperazine acceptor for the asymmetric synthesis of homochiral α-amino acids

Addition of a range of organocuprates to (S)-N,N′-bis(p-methoxybenzyl)-3-methylene-6-isopropylpiperazine-2, 5-dione 8 affords cis-3-isopropyl-6-alkyldiketopiperazines in excellent yield and >95% de. Subsequent deprotection and hydrolysis of these cis-3-isopropyl-6-alkyldiketopiperazines affords homochiral (S)-α-amino acids in excellent yield.

Synthesis of Non-proteinogenic Amino-Acid Methyl Esters with Acid-Sensitive Side Chains from a Chiral Glycine Derivative

A superior chiral glycine derivative 1 (tert-butyl 2-(tert-butyl)-4-methoxy-2,5-dihydro-1,3-imidazole-1-carboxylate, BDI) for the synthesis of acid-sensitive and highly hindered α-amino-acid methyl esters is readily available by resolution methods.The heterocycle 1 is alkylated once and twice in the 5-position with very high diastereoselectivity, and the resulting products (2, 3) are hydrolyzed under very mild conditions to give methyl esters of the corresponding amino acids (6-10).