145149-48-0

Basic information

• Product Name: N-BOC-D/L-PHENYLALANINOL
• Synonyms: AKOS 91528;N-BOC-D/L-PHENYLALANINOL;Boc-DL-Phenylalaninol;N-(tert-Butoxycarbonyl)-DL-phenylalaninol;(R)-tert-butyl 1-hydroxy-3-phenylpropan-2-ylcarbamate;Carbamic acid,N-[1-(hydroxymethyl)-2-phenylethyl]-, 1,1-dimethylethyl ester;2-(tert-Butoxycarbonylamino)-3-phenyl-1-propanol;tert-Butyl (1-hydroxy-3-phenylpropan-2-yl)carbaMate
• CAS NO: 145149-48-0
• Molecular Formula: C₁₄H₂₁NO₃
• Molecular Weight: 251.32
• Mol File: 145149-48-0.mol

Chemical Properties

• Melting Point: 85.0 to 90.0 °C
• Boiling Point: 410.1 °C at 760 mmHg
• Flash Point: 201.8 °C
• Appearance: /
• Density: 1.085 g/cm³
• Vapor Pressure: 1.84E-07mmHg at 25°C
• Refractive Index: 1.52
• Storage Temp.: Sealed in dry,Room Temperature
• PKA: 12.07±0.46(Predicted)
• CAS DataBase Reference: N-BOC-D/L-PHENYLALANINOL(CAS DataBase Reference)
• NIST Chemistry Reference: N-BOC-D/L-PHENYLALANINOL(145149-48-0)
• EPA Substance Registry System: N-BOC-D/L-PHENYLALANINOL(145149-48-0)

Safety Data

• Safety Statements: 24/25
• Hazardous Substances Data: 145149-48-0(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
N-BOC-D/L-PHENYLALANINOL is used as a chiral building block for the synthesis of various pharmaceuticals. Its presence in the synthesis process allows for the creation of enantiomerically pure compounds, which is crucial for the development of drugs with specific therapeutic effects and reduced side effects.
Used in Agrochemical Industry:
N-BOC-D/L-PHENYLALANINOL is used as a chiral ligand or catalyst in the production of agrochemicals. Its ability to impart chirality and improve the selectivity of chemical reactions contributes to the development of more effective and targeted agrochemicals with reduced environmental impact.
Used in Organic Synthesis:
N-BOC-D/L-PHENYLALANINOL is used as a chiral ligand or catalyst in various organic synthesis processes. Its ability to induce chirality and enhance the selectivity of reactions allows for the production of enantiomerically pure compounds, which are essential in the synthesis of complex organic molecules with specific properties and applications.
Used in Research and Development:
N-BOC-D/L-PHENYLALANINOL is used as a research compound in the development of new synthetic methods, catalysts, and ligands. Its unique properties and reactivity make it a valuable tool for exploring new chemical reactions and processes, ultimately contributing to advancements in the fields of chemistry and materials science.

InChI:InChI=1/C14H21NO3/c1-14(2,3)18-13(17)15-12(10-16)9-11-7-5-4-6-8-11/h4-8,12,16H,9-10H2,1-3H3,(H,15,17)

Upstream product

• 24424-99-5 di-tert-butyl dicarbonate 
• 7524-50-7 methyl (2S)-2-amino-3-phenylpropanoate hydrochloride 
• 63-91-2 L-phenylalanine 
• 51987-73-6 (S)-2-tert-butoxycarbonylamino-3-phenyl-propionic acid methyl ester 
• 104-54-1 3-Phenylpropenol 
• 34619-03-9 tert-butyldicarbonate 
• 1795-98-8 rac-phenylalaninol 
• 4530-18-1 2-(tert-butoxycarbonylamino)-3-phenylpropionic acid 
• 51987-73-6 methyl 2-tert-butoxycarbonylamino-3-phenylpropanoate 
• 7732-18-5 water 
• 823-39-2 dimethyl aminopyridine 
• 541-41-3 chloroformic acid ethyl ester 
• 103289-80-1 (2'S,3E)-methyl 2-benzyl-4-(1-t-butoxycarbonylpyrrolidin-2-yl)but-3-enoate 
• 103289-97-0 (S)-2-((E)-3-Isocyanato-4-phenyl-but-1-enyl)-pyrrolidine-1-carboxylic acid tert-butyl ester 

Downstream Products

• 476352-86-0 [1-benzyl-2-(isoquinolin-7-yloxy)-ethyl]-carbamic acid tert-butyl ester 
• 103127-53-3 N-tert-butyloxycarbonyl-2-amino-3-phenylpropionaldehyde 
• 219717-95-0 (R)-2-(tert-butoxycarbonylamino)-3-phenylpropyl acetate 
• 305859-75-0 tert-butyl (1-(benzylamino)-3-phenylpropan-2-yl)carbamate 
• 142854-40-8 2-azido-1-benzylethylamine 
• 1207472-61-4 (1R,2S,5R)-2-isopropyl-5-methylcyclohexyl (2R,4S)-4-((tert-butoxycarbonyl)amino)-2-methyl-5-phenylpentanoate 
• 1467092-18-7 (1R,2S,5R)-2-isopropyl-5-methylcyclohexyl (2S,4S)-4-((tert-butoxycarbonyl)amino)-2-methyl-5-phenylpentanoate 
• 1435915-79-9 C₂₉H₂₉N₃O₆S 
• 1435915-22-2 C₂₉H₂₇N₃O₆S 

Relevant articles and documents

Synthesis, antiarrhythmic activity, and toxicological evaluation of mexiletine analogues

Four mexiletine analogues have been tested for their antiarrhythmic, inotropic, and chronotropic effects on isolated Guinea pig heart tissues and to assess calcium antagonist activity, in comparison with the parent compound mexiletine. All analogues showed from moderate to high antiarrhythmic activity. In particular, three of them (1b,c,e) were more active and potent than the reference drug, while exhibiting only modest or no negative inotropic and chronotropic effects and vasorelaxant activity, thus showing high selectivity of action. All compounds showed no cytotoxicity and 1b,c,d did not impair motor coordination. All in, these new analogues exhibit an interesting cardiovascular profile and deserve further investigation.

Fluorinated Olefinic Lactams: The Case of Amino Acids - Preparation and Mechanistic Studies

Herein, we report the synthesis of analogues of amino acids with a monofluorovinyl moiety. Interestingly, we have found that cyclization of the obtained products proceeds easily in all cases. The cyclization process has not previously been observed at this reaction stage, and such fluorinated lactams derived from phenylalanine, valine, alanine have not been described before.

Direct Access to Primary Amines from Alkenes by Selective Metal-Free Hydroamination

Direct and selective synthesis of primary amines from easily available precursors is attractive yet challenging. Herein, we report the rapid synthesis of primary amines from alkenes via metal-free regioselective hydroamination at room temperature. Ammonium carbonate was used as ammonia surrogate for the first time, allowing for efficient conversion of terminal and internal alkenes into linear, α-branched, and α-tertiary primary amines under mild conditions. This method provides a straightforward and powerful approach to a wide spectrum of advanced, highly functionalized primary amines which are of particular interest in pharmaceutical chemistry and other areas.

Donor–Acceptor Complex Enables Alkoxyl Radical Generation for Metal-Free C(sp3)–C(sp3) Cleavage and Allylation/Alkenylation

The alkoxyl radical is an essential and prevalent reactive intermediate for chemical and biological studies. Here we report the first donor–acceptor complex-enabled alkoxyl radical generation under metal-free reaction conditions induced by visible light. Hantzsch ester forms the key donor–acceptor complex with N-alkoxyl derivatives, which is elucidated by a series of spectrometry and mechanistic experiments. Selective C(sp3)-C(sp3) bond cleavage and allylation/alkenylation is demonstrated for the first time using this photocatalyst-free approach with linear primary, secondary, and tertiary alkoxyl radicals.

A dual inhibitor of matrix metalloproteinases and a disintegrin and metalloproteinases, [18F]FB-ML5, as a molecular probe for non-invasive MMP/ADAM-targeted imaging

Background Numerous clinical studies have shown a correlation between increased matrix metalloproteinase (MMP)/a disintegrin and metalloproteinase (ADAM) activity and poor outcome of cancer. Various MMP inhibitors (MMPIs) have been developed for therapeutic purposes in oncology. In addition, molecular imaging of MMP/ADAM levels in vivo would allow the diagnosis of tumors. We selected the dual inhibitor of MMPs and ADAMs, ML5, which is a hydroxamate-based inhibitor with affinities for many MMPs and ADAMs. ML5 was radiolabelled with 18F and the newly obtained radiolabelled inhibitor was evaluated in vitro and in vivo. Materials and methods ML5 was radiolabelled by direct acylation with N-succinimidyl-4-[18F]fluorobenzoate ([18F]SFB) for PET (positron emission tomography). The resulting radiotracer [18F]FB-ML5 was evaluated in vitro in human bronchial epithelium 16HBE cells and breast cancer MCF-7 cells. The non-radioactive probe FB-ML5 and native ML5 were tested in a fluorogenic inhibition assay against MMP-2, -9, -12 and ADAM-17. The in vivo kinetics of [18F]FB-ML5 were examined in a HT1080 tumor-bearing mouse model. Specificity of probe binding was examined by co-injection of 0 or 2.5 mg/kg ML5. Results ML5 and FB-ML5 showed high affinity for MMP-2, -9, -12 and ADAM-17; indeed IC50 values were respectively 7.4 ± 2.0, 19.5 ± 2.8, 2.0 ± 0.2 and 5.7 ± 2.2 nM and 12.5 ± 3.1, 31.5 ± 13.7, 138.0 ± 10.9 and 24.7 ± 2.8 nM. Radiochemical yield of HPLC-purified [18F]FB-ML5 was 13-16% (corrected for decay). Cellular binding of [18F]FB-ML5 was reduced by 36.6% and 27.5% in MCF-7 and 16HBE cells, respectively, after co-incubation with 10 μM of ML5. In microPET scans, HT1080 tumors exhibited a low and homogeneous uptake of the tracer. Tumors of mice injected with [18F]FB-ML5 showed a SUVmean of 0.145 ± 0.064 (n = 6) which decreased to 0.041 ± 0.027 (n = 6) after target blocking (p 18F. [18F]FB-ML5 demonstrated rather low binding in ADAM-17 overexpressing cell lines. [18F]FB-ML5 uptake showed significant reduction in the HT1080 tumor in vivo after co-injection of ML5. [18F]FB-ML5 may be suitable for the visualization/quantification of diseases overexpressing simultaneously MMPs and ADAMs.

Synthesis of substituted imidazolines by an Ugi/Staudinger/aza-Wittig sequence

A series of 2-(acetamide-2-yl)-imidazolines (II) with 5 points of diversity were prepared by an Ugi-4CR-Staudinger-aza-Wittig-sequence starting from simple azidoalkylamines. The intramolecular aza-Wittig cyclization between the iminophosphane and the tertiary amide of the Ugi product (I) was effected by short microwave irradiation. Competitive cyclization to the secondary amide was not relevant, however, in some cases subsequent formation of the bicyclic ortho-amidines (III) was observed.

Structure-activity relationships of diamine inhibitors of cytochrome P450 (CYP) 3A as novel pharmacoenhancers, part I: Core region

Ritonavir (RTV), an HIV-1 protease inhibitor (PI), is also a potent mechanism-based inhibitor of human cytochrome P450 3A (CYP3A) and has been widely prescribed as a pharmacoenhancer. As a boosting agent for marketed PIs, it reduces pill burden, and improves compliance. Removal of the hydroxyl group from RTV reduces, but does not eliminate HIV PI activity and does not affect CYP3A inhibition. Herein we report the discovery of a novel series of CYP3A inhibitors that are devoid of antiviral activity. The synthesis and evaluation of analogs with extensive modifications of the 1,4-diamine core along with the structure activity relationships with respect to anti-HIV activity, CYP3A inhibitory activity, selectivity against other CYP enzymes and the human pregnane X receptor (PXR) will be discussed.

Synthesis of proline analogues as potent and selective cathepsin S inhibitors

Cathepsin S is a potential target of autoimmune disease. A series of proline derived compounds were synthesized and evaluated as cathepsin S inhibitors. We discovered potent cathepsin S inhibitors through structure-activity relationship studies of proline analogues. In particular, compound 19-(S) showed promising in vitro/vivo pharmacological activities and properties as a selective cathepsin S inhibitor.

Efficient synthesis of functionalized aziridinium salts

(Chemical Equation Presented) Various aziridinium salts were efficiently prepared from bromination of a series of backbone substituted N,N-bisubstituted β-amino alcohols and isolated via flash column chromatography. The effect of C-substitution, N-substitution, solvent, leaving group, and counter-anions on formation of the isolable aziridinium salts was investigated. 2009 American Chemical Society.

METHOD FOR PRODUCING ALCOHOL BY HYDROGENATING LACTONE AND CARBOXYLIC ACID ESTER IN LIQUID PHASE

Disclosed is a method for producing an alcohol from a lactone or a carboxylic acid ester, which enables to produce an alcohol from a lactone or a carboxylic acid ester under relatively mild conditions with high yield and high catalytic efficiency. This method also enables to produce an optically active alcohol from an optically active lactone or an optically active carboxylic acid ester. Specifically disclosed is a method for producing an alcohol by hydrogen reducing a lactone or a carboxylic acid ester in the presence of a catalyst containing ruthenium and a phosphine compound represented by the following general formula (1): wherein R1 represents a spacer; R2, R3, R4, R5, R6 and R7 independently represent a hydrogen atom, an alkyl group having 1-12 carbon atoms, an aryl group or a heterocyclic group; and R8, R9, R10, R11, R12 and R13 independently represent an alkyl group having 1-12 carbon atoms, an aryl group or a heterocyclic group.