Boc-L-proline
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Boc-L-proline

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N-Boc-L-proline is a useful synthetic intermediate. It is used to synthesize Daclatasvir which nhibits the HCV protein NS5A. Daclatasvir can be used as a drug candidate for the treatment of hepatitis C (HCV).

Category
BOC-Amino Acids
Catalog number
BAT-004320
CAS number
15761-39-4
Molecular Formula
C10H17NO4
Molecular Weight
215.30
Boc-L-proline
Synonyms
Boc-L-Pro-OH; (S)-Boc-pyrrolidine-2-carboxylic acid; N-(tert-Butoxycarbonyl)-L-proline
Appearance
White to off-white powder
Purity
≥ 98% (HPLC)
Density
1.1835 g/cm3(rough estimate)
Melting Point
126-145 °C
Boiling Point
355.52°C (rough estimate)
Storage
Store at 2-8 °C
InChI
InChI=1S/C10H17NO4/c1-10(2,3)15-9(14)11-6-4-5-7(11)8(12)13/h7H,4-6H2,1-3H3,(H,12,13)/t7-/m0/s1
InChI Key
ZQEBQGAAWMOMAI-ZETCQYMHSA-N
Canonical SMILES
CC(C)(C)OC(=O)N1CCCC1C(=O)O
1. Application of 2D EXSY and qNMR Spectroscopy for Diastereomeric Excess Determination Following Chiral Resolution of β-Lactams
Eavan C McLoughlin, John E O'Brien, Cristina Trujillo, Mary J Meegan, Niamh M O'Boyle ChemistryOpen. 2022 Jul 25;e202200119. doi: 10.1002/open.202200119. Online ahead of print.
Trans-β-lactam isomers have garnered much attention as anti-cancer microtubule targeting agents. Currently available synthetic methods are available for the preparation of enantiopure β-lactams and favour isomeric cis/trans β-lactam mixtures. Indirect chiral resolution offers the opportunity for isolation of exclusively enantiopure trans-β-lactams. In this study, liquid chromatography chiral resolution of β-lactams derivatized as diastereomer mixtures with a panel of N-protected amino acids is explored, where N-(Boc)-L-proline served as the optimal chiral derivatising reagent. High-performance liquid chromatography failed to adequately determine diastereomeric excess (de) of resolved diastereomers. Variable temperature, 1 H NMR and 2D EXSY spectroscopic analyses of proline-derivatised diastereomers were successfully employed to characterise equilibrating rotamers of resolved diastereomers and determine their de. Integration of resolved resonances corresponding to H3 and H4 of the β-lactam ring served as a quantitative qNMR tool for the calculation of de following resolution.
2. N-alpha-Aminoacyl Colchicines as Promising Anticancer Agents
Ana Marzo-Mas, Laura Conesa-Milián, Sam Noppen, Sandra Liekens, Eva Falomir, Juan Murga, Miguel Carda, Juan A Marco Med Chem. 2021;17(1):21-32. doi: 10.2174/1573406415666191203112406.
Background: In the last years, many efforts have been made to find colchicine derivatives with reduced toxicity. Additionally, the deregulation of amino acid uptake by cancer cells provides an opportunity to improve anticancer drug effectiveness. Objective: To design new colchicine derivatives with reduced cytotoxicity and enhanced selectivity by means of introducing aminoacyl groups. Methods: 34 colchicine analogues bearing L- and D-amino acid pendants were synthetized and characterized by NMR, IR and MS techniques. Cytotoxicity and antimitotic properties were assessed by spectrophotometry and cell cycle assays. Oncogene downregulation was studied by RTqPCR whereas in vivo studies were performed in SCID mice. Results: Compounds exhibit high antiproliferative activities at the nanomolar level while being, in general, less cytotoxic than colchicine. Most compounds inhibit the polymerization of tubulin in a way similar to colchicine itself, with L-amino acid derivatives being the most active in the inhibition of tubulin polymerization. All selected compounds caused cell cycle arrest at the G2/M phase when tested at 1 μM. More specifically, Boc-L-proline derivative 6 arrested half of the population and showed one of the highest Selectivity Indexes. Derivatives 1 (Boc-glycine), 27 (D-leucine) and 31 (Boc-glycine-glycine) proved fairly active in downregulating the expression of the c-Myc, hTERT and VEGF oncogenes, with compound 6 (Boc-L-proline) having the highest activity. This compound was shown to exert a potent anti-tumor effect when administered intraperitoneally (LD50 > 100 mg/kg for 6, compared with 2.5 mg/kg for colchicine). Conclusion: Compound 6 offers an opportunity to be used in cancer therapy with less toxicity problems than colchicine.
3. Enantioselective A3-Coupling Reaction Employing Chiral CuI- iPrpyboxdiPh/ N-Boc-(l)-Proline Complex under Cooperative Catalysis: Application in the Synthesis of (Indol-2-yl)methanamines
Sivasankaran Dhanasekaran, Vinod K Kannaujiya, Rayhan G Biswas, Vinod K Singh J Org Chem. 2019 Mar 15;84(6):3275-3292. doi: 10.1021/acs.joc.8b03225. Epub 2019 Feb 27.
An efficient route to enantioenriched propargylamines via a three-component alkynylation reaction using cooperative catalysis with a CuI- iPrpyboxdiPh complex and N-Boc-(l)-proline has been accomplished. A variety of functionalized amines, aldehydes, and 2-ethynyl anilines were reacted smoothly at ambient temperature to furnish a wide range of propargylamines in high yields (up to 94%) and excellent enantioselectivities (up to 98% ee). Synthetic utility of the methodology has been demonstrated by transforming the products into various synthetically useful intermediates. Finally, propargylamines were transformed into biologically important (indol-2-yl)methanamines over two steps in good yields (up to 88%) with an excellent level of enantioselectivities (up to 95%).
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