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
• Article Data: 19

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

General Description

N-BOC-D/L-PHENYLALANINOL, also known as N-t-butyloxycarbonyl-D/L-phenylalaninol, is a chemical compound derived from the amino acid phenylalanine. It is commonly used in organic synthesis as a chiral ligand or catalyst, as well as a building block in the production of pharmaceuticals and agrochemicals. The compound is a white to off-white solid, and it is typically stored and handled in a dry, cool, and well-ventilated area. N-BOC-D/L-PHENYLALANINOL is an important component in the development and production of various drugs and industrial chemicals due to its ability to impart chirality and improve the selectivity of chemical reactions.

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 
• 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 
• 103289-78-7 (S)-2-((E)-3-Methoxycarbonyl-propenyl)-pyrrolidine-1-carboxylic acid tert-butyl ester 
• 207915-32-0 (2'S,3E)-2-benzyl-4-(1-t-butoxycarbonylpyrrolidin-2-yl)but-3-enoic acid 

Downstream Products

• 103127-53-3 N-tert-butyloxycarbonyl-2-amino-3-phenylpropionaldehyde 
• 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 

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.

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.

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.