PMK ethyl glycidate - C13H14O5

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Cayman Chemical's mission is to enable scientific research that improves human and animal health globally. We are committed to providing researchers with essential, affordable, and high-quality research tools.

Our team of scientists excels in the synthesis, purification, and characterization of a wide range of biochemicals, from small drug-like molecules to complex biolipids and fatty acids. Additionally, we offer extensive expertise in assay development, antibody creation, protein expression, crystallization, and structure determination.

We possess over three decades of research excellence in lipid biochemistry, which includes studies on arachidonic acid cascades, inositol phosphates, and cannabinoids. This foundational knowledge has allowed us to produce top-tier reagents for a multitude of research areas including cancer, oxidative stress, epigenetics, neuroscience, inflammation, and metabolism.

Our laboratory is adept at rapidly developing manufacturing processes and analytical methods, facilitating both clinical and commercial GMP-API production. We are currently focusing on pre-clinical drug discovery in areas like bone restoration, muscular dystrophy, oncology, and inflammation. Our highly skilled Ph.D.-level scientists provide comprehensive Hit-to-Lead Discovery and Profiling Services for epigenetic targets. Our talented chemists can be contracted for complete sample analysis for numerous analytes measured by our assays. Additionally, we offer a wide array of analytical services employing techniques such as LC-MS/MS, HPLC, and GC.

Accreditations
ISO/IEC 17025:2005
ISO Guide 34:2009

Cayman is a forefront provider of high-purity Schedule I-V Controlled Substances to federally-licensed and academic research institutions for forensic analyses. We hold dual accreditation from ACLASS Accreditation Services under ISO/IEC 17025:2005 and ISO Guide 34:2009 standards.

General description

PMK ethyl glycidate can be used as an intermediate in organic synthesis and pharmaceutical development, primarily utilized in laboratory R&D and pharmaceutical production.

Synthetic routes

Additional reading:
Nanosilver in Biomedicine: Advantages and Restrictions

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Fig. 1 The synthetic step 1 of PMK ethyl glycidate.

To a solution of piperonal (1, 3.00 g, 19.9 mmol) in CH₂Cl₂ (100 mL), (carbethoxyethylidene)triphenylphosphorane (2,14.5 g, 40.0 mmol) was added, and the reaction mixture was stirred for 24 h at room temperature. The mixture was then concentrated at reduced pressure, and the residue was purified by flash column chromatography on silica gel (hexanes/EtOAc,10:1) to yield olefin 3 (4.45 g, 95%) as a colorless oil: 1H NMR (400 MHz, CDCl3) d 7.58 (s, 1H), 6.92 (d, J = 1.7 Hz, 1H), 6.90 (dd, J = 7.9, 1.7 Hz, 1H), 6.82 (d, J = 8.0 Hz, 1H), 5.97 (s, 2H), 4.24 (q, J = 7.1 Hz, 2H), 2.10 (d, J = 1.6 Hz, 3H),1.33 (t, J = 7.1 Hz, 3H); 13C NMR (100 MHz, CDCl3) d 168.7,147.6, 138.3, 129.9, 126.9, 124.6, 109.5, 108.2, 101.2, 60.7, 14.3,1 4.0; IR (ATR, cm^-1): 2981, 2902,1698, 1628, 1502, 1489,1442, 1258, 1224; HRMS (EI) m/z calcd for C₁₃H₁₄O₄ (M⁺) 234.0892, found 234.0895 [1].

Fig. 2 The synthetic step 2 of PMK ethyl glycidate.

To a solution of olefin 3 (3.00 g, 12.8 mmol) in CH₂Cl₂ (80 mL) was added 50–55% m-chloroperbenzoic acid (6.2 g,17.9 mmol). The reaction mixture was refluxed for 24 h, cooled to room temperature, quenched with 10% aqueous sodium sulfite (30 mL), and diluted with CH₂Cl₂ (100 mL). The organic layer was separated, and the aqueous layer was extracted with CH₂Cl₂ (2 × 30 mL). The combined organic layers were washed with saturated aqueous NaHCO₃ and brine, dried over anhydrous MgSO₄, and concentrated at reduced pressure. The resulting residue was purified by flash column chromatography on silica gel (hexanes/EtOAc, 10:1) to afford epoxide 4 (2.12 g, 66%) as a colorless oil: 1H NMR (400 MHz, CDCl3) d 6.79 (d, J = 1.6 Hz, 2H), 6.76 (s, 1H), 5.96 (d, J = 1.6 Hz, 2H), 4.30–4.17 (m, 2H), 4.21 (s, 1H), 1.31 (ddd, J = 8.8, 8.8, 1.7 Hz, 6H); 13C NMR (100 MHz, CDCl3) d 170.8, 147.7, 147.6, 127.6, 120.3, 108.2, 107.0, 101.2, 62.2, 61.8, 59.9, 14.1, 12.5; IR (ATR, cm^-1) 2982, 2903, 1726, 1504, 1492, 1444, 1281, 1240; HRMS (EI) m/z calcd for C₁₃H₁₄O₅ (M⁺) 250.0841, found 250.0837 [1].

Application

As an intermediate in organic synthesis

PMK ethyl glycidate serves as an intermediate in the synthesis of M-ALPHA analogs and MDMA. The widespread abuse of illicit psychoactive substances poses serious public health challenges. For example, a suspicious package seized by Korean customs revealed two psychoactive substances, one being the well-known MDMA ("Ecstasy"), identified through chromatography and mass spectrometry methods. The other was an M-ALPHA analog, which though not yet assessed for psychoactivity, warrants attention as a potential new psychoactive substance or MDMA byproduct [1].

PMK ethyl glycidate also functions as an intermediate in synthesizing desoxy phenethylamine analogs. These analogs, derived from piperonal, feature varying side-chains and cyclic amines, such as azetidine, pyrrolidine, piperidine, and azepane. These compounds have identical elemental compositions and key mass spectral fragment ions. Individual analogs and their regioisomers are effectively separated in gas chromatography, indicating the nuanced differences between aminoketones and desoxyamines [2].

References

[1] Lee J H, Park O R, Mandava S, et al. Identification of a new M-ALPHA analog and MDMA in an illegal health product[J]. Forensic science international, 2020, 313: 110332.

[2] Abiedalla Y, DeRuiter J, Clark C R. GC–MS, GC–MS/MS and GC-IR differentiation of desoxy cathinone derivatives: cyclic tertiary amines related to MDPV[J]. Journal of Chromatography B, 2017, 1048: 38-48.

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