51372-93-1

Basic information

• Product Name: BOC-MET-OL
• Synonyms: N-ALPHA-T-BOC-L-METHIONINOL;N-BOC-L-METHIONINOL;N-(TERT-BUTOXYBUTOXYCARBONYL)-L-METHIONINOL;N-T-BUTOXYCARBONYL-L-METHIONINOL;BOC-L-METHIONINOL;BOC-MET-OL;BOC-METHIONINOL;BOC-(S)-2-AMINO-4-METHYLTHIO-1-BUTANOL
• CAS NO: 51372-93-1
• Molecular Formula: C₁₀H₂₁NO₃S
• Molecular Weight: 235.34
• Product Categories: Amino Acid Derivatives;Amino Acids
• Mol File: 51372-93-1.mol

Chemical Properties

• Melting Point: 48.0 to 52.0 °C
• Boiling Point: 370.868 °C at 760 mmHg
• Flash Point: 178.095 °C
• Appearance: /
• Density: 1.081 g/cm³
• Storage Temp.: Store at 0°C
• CAS DataBase Reference: BOC-MET-OL(CAS DataBase Reference)
• NIST Chemistry Reference: BOC-MET-OL(51372-93-1)
• EPA Substance Registry System: BOC-MET-OL(51372-93-1)

Safety Data

• Hazard Codes: T
• Statements: 25
• Safety Statements: 45
• RIDADR: UN 2811 6.1 / PGIII
• Hazardous Substances Data: 51372-93-1(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
BOC-MET-OL is used as a protecting agent for the amino acid methionine to temporarily block its reactive sites during chemical reactions and synthesis processes. This protection is crucial for the successful production of peptide and protein-based drugs and the development of innovative pharmaceuticals.
Used in Peptide and Protein-based Drug Production:
BOC-MET-OL is employed as a crucial component in the synthesis of peptide and protein-based drugs, ensuring the preservation of methionine's functional groups and facilitating the successful assembly of complex molecular structures.
Used in Novel Pharmaceutical Development:
In the quest for new pharmaceuticals, BOC-MET-OL plays a significant role as a protecting agent, enabling chemists to manipulate and synthesize intricate molecular structures with greater precision and efficiency. Its compatibility with diverse reaction conditions further enhances its utility in the development of cutting-edge pharmaceuticals.

Upstream product

• 24424-99-5 di-tert-butyl dicarbonate 
• 2899-37-8 (S)-methioninol 
• 33900-24-2 N-(tert-butoxycarbonyl)-L-methionine methyl ester 
• 76220-80-9 N-Boc-(S)-methionine ethyl ester 
• 2488-15-5 N-tert-butoxycarbonyl-L-methionine 
• 63-68-3 L-methionine 
• 27067-02-3 N-Boc-(S)-methionine ethyl ester p-toluenesulphonic acid salt 
• 34619-03-9 tert-butyldicarbonate 
• 10332-17-9 Met-OMe 
• 84890-95-9 C₁₅H₂₇NO₆S 

Downstream Products

• 76220-79-6 (S)-tert-butyl 2-(1-tosyloxy-4-methylthio)butylcarbamate 
• 1380243-28-6 C₁₆H₂₂F₃NO₂S 
• 1048703-14-5 (R)-tert-butyl (4-hydroxy-1-(2,4,5-trifluorophenyl)butan-2-yl)carbamate 
• 486460-00-8 (3R)-3-[(1,1-dimethylethoxycarbonyl)amino]-4-(2,4,5-trifluorophenyl)butanoic acid 
• 486460-23-5 (R)-tert-butyl 4-oxo-4-(3-(trifluoromethyl)-5,6-dihydro-[1,2,4]triazolo[4,3-a]pyrazin-7(8H)-yl)-1-(2,4,5-trifluorophenyl)butan-2-ylcarbamate 
• 354153-37-0 1,1-dimethylethyl [(1S)-1-({[(1,1-dimethylethyl)(diphenyl)silyl]oxy}methyl)prop-2-en-1-yl]carbamate 
• 852616-64-9 tert-butyl (S)-2-{[(tert-butyldiphenylsilyl)oxy]methyl}-2,5-dihydro-1H-pyrrole-1-carboxylate 
• 852616-66-1 tert-butyl (2R,3R,4S)-2-{[(tert-butyldiphenylsilyl)oxy]methyl}-3,4-dihydroxypyrrolidine-1-carboxylate 
• 933055-19-7 tert-butyl (3aR,4R,6aS)-4-{[(tert-butyldiphenylsilyl)oxy]methyl}-2,2-dimethyltetrahydro-5H-[1,3]dioxolo[4,5-c]pyrrole-5-carboxylate 

Relevant articles and documents

Design, synthesis and biological evaluation of isoxazole-based CK1 inhibitors modified with chiral pyrrolidine scaffolds

In this study, we report on the modification of a 3,4-diaryl-isoxazole-based CK1 inhibitor with chiral pyrrolidine scaffolds to develop potent and selective CK1 inhibitors. The pharmacophore of the lead structure was extended towards the ribose pocket of

Synthesis, biological evaluation, and molecular modeling studies of chiral chloroquine analogues as antimalarial agents

In a focused exploration, we designed, synthesized, and biologically evaluated chiral conjugated new chloroquine (CQ) analogues with substituted piperazines as antimalarial agents. In vitro as well as in vivo studies revealed that compound 7c showed potent activity (in vitro 50% inhibitory concentration, 56.98 nM for strain 3D7 and 97.76 nM for strain K1; selectivity index in vivo [up to at a dose of 12.5 mg/kg of body weight], 3,510) as a new lead antimalarial agent. Other compounds (compounds 6b, 6d, 7d, 7h, 8c, 8d, 9a, and 9c) also showed moderate activity against a CQ-sensitive strain (3D7) and superior activity against a CQ-resistant strain (K1) of Plasmodium falciparum. Furthermore, we carried out docking and three-dimensional quantitative structure-activity relationship (3D-QSAR) studies of all in-house data sets (168 molecules) of chiral CQ analogues to explain the structure-activity relationships (SAR). Our new findings specify the significance of the H-bond interaction with the side chain of heme for biological activity. In addition, the 3D-QSAR study against the 3D7 strain indicated the favorable and unfavorable sites of CQ analogues for incorporating steric, hydrophobic, and electropositive groups to improve the antimalarial activity.

Synthesis and evaluation of chirally defined side chain variants of 7-chloro-4-aminoquinoline to overcome drug resistance in malaria chemotherapy

A novel 4-aminoquinoline derivative [(S)-7-chloro-N-(4-methyl-1-(4-methyl-piperazin-1-yl)pentan-2-yl)-quinolin-4-amine triphosphate] exhibiting curative activity against chloroquine-resistant malaria parasites has been identified for preclinical development as a blood schizonticidal agent. The lead molecule selected after detailed structure-activity relationship (SAR) studies has good solid-state properties and promising activity against in vitro and in vivo experimental malaria models. The in vitro absorption, distribution, metabolism, and excretion (ADME) parameters indicate a favorable drug-like profile.

Overcoming mutagenicity and ion channel activity: Optimization of selective spleen tyrosine kinase inhibitors

Development of a series of highly kinome-selective spleen tyrosine kinase (Syk) inhibitors with favorable druglike properties is described. Early leads were discovered through X-ray crystallographic analysis, and a systematic survey of cores within a selected chemical space focused on ligand binding efficiency. Attenuation of hERG ion channel activity inherent within the initial chemotype was guided through modulation of physicochemical properties including log D, PSA, and pKa. PSA proved most effective for prospective compound design. Further profiling of an advanced compound revealed bacterial mutagenicity in the Ames test using TA97a Salmonella strain, and subsequent study demonstrated that this mutagenicity was pervasive throughout the series. Identification of intercalation as a likely mechanism for the mutagenicity-enabled modification of the core scaffold. Implementation of a DNA binding assay as a prescreen and models in DNA allowed resolution of the mutagenicity risk, affording molecules with favorable potency, selectivity, pharmacokinetic, and off-target profiles.

Design, synthesis and evaluation of novel indole derivatives as AKT inhibitors

Herein, we describe the discovery and synthesis of a new series of 1,2,4,7-tetra-substituted indole derivatives as novel AKT inhibitors by optimization of a weak hit methyl 4-(2-aminoethoxy)-1H-indole-2-carboxylate (1). Both representative compounds 6a and 6o exhibited the most potent inhibitory activities against AKT1, with inhibition rates of 72.5% and 78.6%, respectively, at concentrations of 10 nM. In addition, compounds 6a and 6o also potently inhibited the phosphorylation of the downstream GSK3 protein and displayed slightly better anti-proliferative activities in a prostate cancer cell line.

A rapid entry to amino acid derived diverse 3,4-dihydropyrazines and dihydro[1,2,3]triazolo[1,5-a]pyrazines through 1,3-dipolar cycloaddition

An efficient, general and practical synthesis of diverse 3,4-dihydropyrazines, 6,7-dihydro-[1,2,3]triazolopyrazines and 7,8-dihydro-[1,2,3]triazolodiazepines through intramolecular 1,3-dipolar cycloaddition from amino acid derived common intermediates with high yields is described. Moreover, one-pot access to optically active 3-aryl substituted 6,7-dihydro-[1,2,3]triazolo[1,5-a]pyrazines in the palladium-copper co-catalytic system has also been achieved in this work. The easy substrate availability and operational simplicity make the process suitable for further exploration. This journal is the Partner Organisations 2014.

New orally active dual enkephalinase inhibitors (DENKIs) for central and peripheral pain treatment

Protecting enkephalins, endogenous opioid peptides released in response to nociceptive stimuli, is an innovative approach for acute and neuropathic pain alleviation. This is achieved by inhibition of their enzymatic degradation by two membrane-bound Zn-metallopeptidases, neprilysin (NEP, EC 3.4.24.11) and aminopeptidase N (APN, EC 3.4.11.2). Selective and efficient inhibitors of both enzymes, designated enkephalinases, have been designed that markedly increase extracellular concentrations and half-lives of enkephalins, inducing potent antinociceptive effects. Several chemical families of Dual ENKephalinase Inhibitors (DENKIs) have previously been developed but devoid of oral activity. We report here the design and synthesis of new pro-drugs, derived from co-drugs combining a NEP and an APN inhibitor through a disulfide bond with side chains improving oral bioavailability. Their pharmacological properties were assessed in various animal models of pain targeting central and/or peripheral opioid systems. Considering its efficacy in acute and neuropathic pain, one of these new DENKIs, 19-IIIa, was selected for clinical development.

INTERMEDIATES OF SITAGLIPTIN AND PREPARATION PROCESS THEREOF

Disclosed are intermediates of Sitagliptin, a preparation process thereof, and a process for synthesizing Sitagliptin using these intermediates. Sitagliptin is synthesized by using chiral amino compounds as a raw material, without having to build a chiral center with a chiral asymmetric catalytic hydrogenation, and high-pressure hydrogenation is avoided.

INTERMEDIATES OF SITAGLIPTIN AND PREPARATION PROCESS THEREOF

Disclosed are intermediates of Sitagliptin, a preparation process thereof, and a process for synthesizing Sitagliptin using these intermediates. Sitagliptin is synthesized by using chiral amino compounds as a raw material, without having to build a chiral center with a chiral asymmetric catalytic hydrogenation, and high-pressure hydrogenation is avoided.

Simple and rapid synthesis of Nα-urethane protected β-amino alcohols and peptide alcohols employing HATU

The activation of the Nα--urcihanc protected (Fmoc-/Boc-/Z-/Bsmoc) α-amino acids employing l-[bis(dimethylamino)- methylene]-lH-l,2,3-triazolo-[4,5-6]pyridinium.0hexa-flurophosphate-3-oxide (HATU) followed by reduction of the in situ generated -OAt ester with NaBH 4 results in the corresponding ss-amino alcohols in good yields. This synthesis is the first demonstration of the application of the efficient coupling agent HATU for practical synthesis of ss-amino alcohols. The protocol is general for all common N-protecting groups including the highly base sensitive Bsmoc group. The protocol has also been successfully extended for the synthesis of peptide alcohols.