37592-53-3

Basic information

• Product Name: L-serine isopropyl ester hydrochloride
• Synonyms: L-serine isopropyl ester hydrochloride
• CAS NO: 37592-53-3
• Molecular Weight: 183.635
• Mol File: 37592-53-3.mol

Chemical Properties

• CAS DataBase Reference: L-serine isopropyl ester hydrochloride(CAS DataBase Reference)
• NIST Chemistry Reference: L-serine isopropyl ester hydrochloride(37592-53-3)
• EPA Substance Registry System: L-serine isopropyl ester hydrochloride(37592-53-3)

Safety Data

• Hazardous Substances Data: 37592-53-3(Hazardous Substances Data)

Upstream product

• 1253690-12-8 N-tert-butoxycarbonyl-L-serine isopropyl ester 
• 56-45-1 L-serin 
• 75-29-6 isopropyl chloride 
• 67-63-0 isopropyl alcohol 

Downstream Products

• 53517-65-0 (-)-serine isopropyl ester 
• 84028-54-6 (S)-isopropyl 2-(2-(benzyloxy)phenyl)-2-oxazoline-4-carboxylate 
• 609366-79-2 (R)-(+)-isopropyl-2-benzamido-3-iodopropanoate 
• 609366-82-7 (R)-(+)-isopropyl-2-benzamido-3-bromopropanoate 
• 609366-73-6 (S)-(+)-2-phenyl-4-isopropyloxycarbonyl-2-oxazoline 
• 84028-52-4 L-N-(2-(benzyloxy)benzoyl)serine isopropyl ester 
• 37592-60-2 (S)-2-(2-hydroxy-phenyl)-4,5-dihydro-oxazole-4-carboxylic acid isopropyl ester 

Relevant articles and documents

Metal-to-Ligand Ratio-Dependent Chemodivergent Asymmetric Synthesis

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The reactions of α-amino acids and α-amino acid esters with high valent transition metal halides: synthesis of coordination complexes, activation processes and stabilization of α-ammonium acylchloride cations

Titanium tetrachloride smoothly reacted with a selection of α-amino acids (aaH) in CH2Cl2 affording yellow to orange solid coordination compounds, 1a-d, in 70-78% yields. The salts [NHEt3][TiCl4(aa)], 2a-b, were obtained from TiCl4/aaH/NEt3 (aa = l-phenylalanine, N,N-dimethylphenylalanine), in 60-65% yields. The complex , 3, was isolated from the reaction of l-proline with NbCl5/NHiPr2, performed in CH2Cl2 at room temperature. The X-ray structure of 3 features a bridging (E)-1,2-bis(3,4-dihydro-2H-pyrrol-5-yl)ethene-1,2-diolate ligand, resulting from the unprecedented C-C coupling between two proline units. Unusually stable α-ammonium acyl chlorides were prepared by the reactions of PCl5/MCln (MCln = NbCl5, WCl6) with l-proline, N,N-dimethylphenylalanine, sarcosine and l-methionine. MX5 (M = Nb, Ta; X = F, Cl) reacted with l-leucine methylester and l-proline ethylester to give ionic coordination compounds, [MX4L2][MX6] (M = Nb, L = Me2CHCH2CH(NH2)CO2Me, X = F, 9; Cl, 11a; M = Nb, X = Cl, , 11c; Ta, 11d), in moderate to good yields. [NbCl5(Me2CHCH2CHNH3CO2Me)][NbCl6], 12, was isolated as a co-product of the reaction of NbCl5 with l-leucine isopropylester, and crystallographically characterized. The reaction of NbCl5 with l-serine isopropylester afforded NbCl3(OCH2CHNHCO2iPr), 13, in 66% yield. The activation of the ester O-R bond was observed in the reactions of l-leucine methyl ester with NbF5 and l-proline ethyl ester with MBr5 (M = Nb, Ta), these reactions proceeding with the release of EtF and EtBr, respectively. All the metal products were characterized by analytical and spectroscopic methods, while DFT calculations were carried out in order to provide insight into the structural and mechanistic aspects.

Discovery of biphenyl imidazole derivatives as potent antifungal agents: Design, synthesis, and structure-activity relationship studies

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A series of monomers based on the methyl, ethyl, and isopropyl esters of Nα-(methacryloyl)-serine and -threonine were synthesized, and used in an AIBN-initiated radical polymerization reaction to yield polymers with an Mn ranging between 6.6 and 23.8 kDa. The newly synthesized polymers showed LCST behavior in aqueous solution that could be tailored by subtle variations of the hydrophobicity of the monomers to obtain a broad range of cloud points between 1.5 and >100°C. According to HPLC, the hydrolytic t1/2-values (pH 7.4 at 37°C) of the monomers were found to be 5, 12, and 40 days of the methyl, ethyl, and isopropyl esters, respectively, while the hydrolysis rate of poly[Nα-(methacryloyl)-Ser-OMe] and poly[Nα-(methacryloyl)-Thr-OMe] was found to be significantly lower compared to the corresponding monomers. In order to obtain thermoresponsive nanoparticles, Nα-(methacryloyl)-Thr-OEt was polymerized with (PEG monomethyl ether 5000)2-ABCPA as macroinitiator to yield an amphiphilic block co-polymer, poly[Nα-(methacryloyl)-Thr-OEt]-b-(PEG monomethyl ether 5000), which forms particles of 300 nm at a temperature higher than its cloud point of 24°C. Incubation at physiological conditions induced ester hydrolysis resulting in a destabilization of the particles making these particles suitable for drug delivery purposes.

Synthesis of ester prodrugs of 9-(S)-[3-Hydroxy-2-(phosphonomethoxy)propyl] -2,6-diaminopurine (HPMPDAP) as anti-poxvirus agents

9-(S)-[3-Hydroxy-2-(phosphonomethoxy)propyl]-2,6-diaminopurine (HPMPDAP) and its cyclic form were selected for further evaluation as potential drug candidates against poxvirus infections. To increase bioavailability of these compounds, synthesis of their structurally diverse ester prodrugs was carried out: alkoxyalkyl (hexadecyloxypropyl, octadecyloxyethyl, hexadecyloxyethyl), pivaloyloxymethyl (POM), 2,2,2-trifluoroethyl, butylsalicylyl, and prodrugs based on peptidomimetics. Most HPMPDAP prodrugs were synthesized in the form of monoesters as well as the corresponding cyclic phosphonate esters. The activity was evaluated not only against vaccinia virus but also against different herpes viruses. The most potent and active prodrugs against vaccinia virus were the alkoxyalkyl ester derivatives of HPMPDAP, with 50% effective concentrations 400-600-fold lower than those of the parent compound. Prodrugs based on peptidomimetics, the 2,2,2-trifluoroethyl, the POM, and the butylsalicylyl derivatives, were able to inhibit vaccinia virus replication at 50% effective concentrations that were equivalent or ～10-fold lower than those observed for the parent compounds.