125347-83-3

Usage

Uses

Used in Organic Synthesis:
BOC-DL-PROLINE ETHYL ESTER is used as a protecting group in peptide synthesis for its ability to be easily removed under mild acidic conditions, facilitating the synthesis of complex peptide structures.
Used in Pharmaceutical Production:
In the pharmaceutical industry, BOC-DL-PROLINE ETHYL ESTER is utilized as a building block for the production of various pharmaceuticals, contributing to the development of new drugs and therapeutic agents.
Used in Medicinal Chemistry and Drug Development:
BOC-DL-PROLINE ETHYL ESTER plays a significant role in medicinal chemistry, where it is employed in the creation of diverse peptide-based drugs and therapeutic agents, enhancing the scope of treatment options for various diseases and conditions.

Upstream product

• 15761-39-4 1-(tert-butoxycarbonyl)-L-proline 
• 75-03-6 ethyl iodide 
• 194594-23-5 5-hydroxy-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-ethyl ester 
• 24424-99-5 di-tert-butyl dicarbonate 
• 33305-75-8 L-proline ethyl ester monohydrochloride 
• 64-17-5 ethanol 
• 147-85-3 L-proline 
• 144978-35-8 (S)-ethyl N-tert-butoxycarbonylpyroglutamate 
• 5817-26-5 ethyl (2S)-pyrrolidine-2-carboxylate 
• 161362-39-6 ethyl 6-ethoxy-1,2-oxazinane-3-carboxylate 
• 60169-67-7 ethyl pyrrolidine-2-carboxylate 
• 161362-39-6 ethyl cis-6-ethoxy-1,2-oxazinane-3-carboxylate 
• 112135-47-4 ethyl 6-ethoxy-5,6-dihydro-4H-1,2-oxazine-3-carboxylate 
• 161362-39-6 (3S,6S)-6-Ethoxy-[1,2]oxazinane-3-carboxylic acid ethyl ester 

Downstream Products

• 1621435-13-9 tert-butyl 2-(((2S, 3R)-1, 3-bis (benzyloxy)-1-oxobutan-2-yl) carbamoyl)-2-(hydroxymethyl) pyrrolidine-1-carboxylate 
• 1621435-28-6 tert-butyl 2-((2S, 3R)-1, 3-bis (benzyloxy)-1-oxobutan-2-yl)-1-oxo-2, 5-diazaspiro [3.4] octane-5-carboxylate 
• 1194030-71-1 2-((benzyloxy)methyl)-1-(tert-butoxycarbonyl)pyrrolidine-2-carboxylic acid 
• 1621482-38-9 1-tert-butyl 2-ethyl 2-((benzyloxy)methyl)pyrrolidine-1,2-dicarboxylate 
• 1621435-37-7 tert-butyl 2-(((2S,3R)-1,3-bis(benzyloxy)-1-oxobutan-2-yl)carbamoyl)-2-(1-hydroxyethyl)pyrrolidine-1-carboxylate 
• 1621435-38-8 tert-butyl 2-((2S,3R)-1,3-bis(benzyloxy)-1-oxobutan-2-yl)-1-methyl-3-oxo-2,5-diazaspiro[3.4]octane-5-carboxylate 
• 1621435-94-6 tert-butyl 2-((2S,3R)-1-amino-3-hydroxy-1-oxobutan-2-yl)-1-methyl-3-oxo-2,5-diazaspiro[3.4]octane-5-carboxylate 
• 1621436-01-8 tert-butyl 2-(((2S,3R)-3-(benzyloxy)-1-oxo-1-(pyrrolidin-1-yl)butan-2-yl)carbamoyl)-2-(1-hydroxyethyl)pyrrolidine-1-carboxylate 
• 1621436-02-9 tert-butyl 2-((2S,3R)-3-(benzyloxy)-1-oxo-1-(pyrrolidin-1-yl)butan-2-yl)-1-methyl-3-oxo-2.5-diazaspiro[3.4]octane-5-carboxylate 
• 173690-69-2 tert-butyl 2-(2-cyanoacetyl)pyrrolidine-1-carboxylate 

Relevant academic research and scientific papers

Highly Chemoselective Reduction of N-Boc Protected Lactams

N-Boc protected lactams can be reduced chemoselectively in the presence of other groups such as esters, nitriles carbamates or double bonds by first reducing the amide carbonyl group into the corresponding hemiaminal using lithium triethylborohydride foll

Catalytic Synthesis of N-Heterocycles via Direct C(sp3)-H Amination Using an Air-Stable Iron(III) Species with a Redox-Active Ligand

Coordination of FeCl3 to the redox-active pyridine-aminophenol ligand NNOH2 in the presence of base and under aerobic conditions generates FeCl2(NNOISQ) (1), featuring high-spin FeIII and an NNOISQ radical ligand. The complex has an overall S = 2 spin state, as deduced from experimental and computational data. The ligand-centered radical couples antiferromagnetically with the Fe center. Readily available, well-defined, and air-stable 1 catalyzes the challenging intramolecular direct C(sp3)-H amination of unactivated organic azides to generate a range of saturated N-heterocycles with the highest turnover number (TON) (1 mol% of 1, 12 h, TON = 62; 0.1 mol% of 1, 7 days, TON = 620) reported to date. The catalyst is easily recycled without noticeable loss of catalytic activity. A detailed kinetic study for C(sp3)-H amination of 1-azido-4-phenylbutane (S1) revealed zero order in the azide substrate and first order in both the catalyst and Boc2O. A cationic iron complex, generated from the neutral precatalyst upon reaction with Boc2O, is proposed as the catalytically active species.

Practical synthesis of ethyl 3-fluoro-1-pyrrole-2-carboxylate: A key fragment of a potent drug candidate against hepatitis b virus

We report herein the development of two efficient synthetic routes for the preparation of a key fragment required for the synthesis of potent drug candidates of Hepatitis B virus. The ethyl 3-fluoro-1-H-pyrrole-2-carboxylate scaffold was synthesized from readily available starting materials in good overall yields. The scalability of one of the developed routes was demonstrated and afforded the desired target in good yield and excellent purity (99%).

ANTIVIRAL COMPOUNDS

The present disclosure provides compounds for treating a variety of diseases, such as respiratory syncytial virus (RSV), HRV, hMPV, ebola, Zika, West Nile, Dengue, and HCV.

A (1 R, 3 S) -3 - amino-cyclopentanol hydrochloride preparation method (by machine translation)

The invention discloses a (1 R, 3 S) - 3 - amino-cyclopentanol hydrochloride of the preparation method, the method using chiral carboxylic acid with hydroxylamine to form the amide as chiral source, in copper catalyzed oxidation in the reaction system to rapidly obtain a chiral Diels - alder reaction product, after passes through the reduction reaction and alkaline deprotection reaction, and acidified after reaction to obtain the target product. Chiral inducing reagent chiral carboxylic acid by simple acidification, extraction processing can be reclaimed and reused. This kind of (1 R, 3 S) - 3 - amino-cyclopentanol hydrochloride preparation method has high operation safety and high selectivity, raw materials are easy, and the cost is low, the reaction time is short and simple process flow and the like. (by machine translation)

An Effective [FeIII(TF4DMAP)Cl] Catalyst for C-H Bond Amination with Aryl and Alkyl Azides

[FeIII(TF4DMAP)Cl] can efficiently catalyze intermolecular sp3 C-H amination using aryl azides and intramolecular sp3 C-H amination of alkyl azides in moderate-to-high product yields. At catalyst loading down to 1 mol %, the reactions display high chemo- and regioselectivity with broad substrate scope and are effective for late-stage functionalization of complex natural/bioactive molecules.

N-Heterocyclic Carbene Iron(III) Porphyrin-Catalyzed Intramolecular C(sp3)–H Amination of Alkyl Azides

Metal-catalyzed intramolecular C?H amination of alkyl azides constitutes an appealing approach to alicyclic amines; challenges remain in broadening substrate scope, enhancing regioselectivity, and applying the method to natural product synthesis. Herein we report an iron(III) porphyrin bearing axial N-heterocyclic carbene ligands which catalyzes the intramolecular C(sp3)–H amination of a wide variety of alkyl azides under microwave-assisted and thermal conditions, resulting in selective amination of tertiary, benzylic, allylic, secondary, and primary C?H bonds with up to 95 % yield. 14 out of 17 substrates were cyclized selectively at C4 to give pyrrolidines. The regioselectivity at C4 or C5 could be tuned by modifying the reactivity of the C5–H bond. Mechanistic studies revealed a concerted or a fast re-bound mechanism for the amination reaction. The reaction has been applied to the syntheses of tropane, nicotine, cis-octahydroindole, and leelamine derivatives.

Cobalt-Porphyrin-Catalysed Intramolecular Ring-Closing C?H Amination of Aliphatic Azides: A Nitrene-Radical Approach to Saturated Heterocycles

Cobalt-porphyrin-catalysed intramolecular ring-closing C?H bond amination enables direct synthesis of various N-heterocycles from aliphatic azides. Pyrrolidines, oxazolidines, imidazolidines, isoindolines and tetrahydroisoquinoline can be obtained in good to excellent yields in a single reaction step with an air- and moisture-stable catalyst. Kinetic studies of the reaction in combination with DFT calculations reveal a metallo-radical-type mechanism involving rate-limiting azide activation to form the key cobalt(III)-nitrene radical intermediate. A subsequent low barrier intramolecular hydrogen-atom transfer from a benzylic C?H bond to the nitrene-radical intermediate followed by a radical rebound step leads to formation of the desired N-heterocyclic ring products. Kinetic isotope competition experiments are in agreement with a radical-type C?H bond-activation step (intramolecular KIE=7), which occurs after the rate-limiting azide activation step. The use of di-tert-butyldicarbonate (Boc2O) significantly enhances the reaction rate by preventing competitive binding of the formed amine product. Under these conditions, the reaction shows clean first-order kinetics in both the [catalyst] and the [azide substrate], and is zero-order in [Boc2O]. Modest enantioselectivities (29–46 % ee in the temperature range of 100–80 °C) could be achieved in the ring closure of (4-azidobutyl)benzene using a new chiral cobalt-porphyrin catalyst equipped with four (1S)-(?)-camphanic-ester groups.

Cobalt-Catalyzed Esterification of Amides

The first cobalt-catalyzed amide activation of N-Boc-amides, and their conversion into esters, is reported here. This new methodology presents a very practical process that does not require an inert atmosphere, uses an inexpensive cobalt catalyst, and proceeds under mild reaction conditions. This catalytic system has a broad substrate scope and has been shown to be highly efficient, with catalyst loadings as low as 1 mol %.

SPIRO-LACTAM NMDA RECEPTOR MODULATORS AND USES THEREOF

Disclosed are compounds having enhanced potency in the modulation of NMDA receptor activity. Such compounds are contemplated for use in the treatment of conditions such as depression and related disorders. Orally available formulations and other pharmaceutically acceptable delivery forms of the compounds, including intravenous formulations, are also disclosed.