144978-12-1

Basic information

• Product Name: BOC-PYR-OET
• Synonyms: (2S)-5-oxo-1,2-pyrrolidinedicarboxylic acid 1-(tert-butyl) 2-ethyl ester;Boc-L-Pyroglutamic acid ethyl ester/ Boc-Pyr-Oet;1-(tert-butyl)2-ethyl(S)-5-oxopyrrolidine-1,2-dicarboxylate;Ethyl (S)-1-Boc-5-oxopyrrolidine-2-carboxy;N-Boc-L-pyroglutamic acid ethyl este;1-BOC-L-PYROGLUTAMIC ACID ETHYL ESTER ;N-Boc-L-pyroglutamic acid ethyl ester;(S)-N-alpha-t-Butyloxycarbonyl-pyroglutamic acid ethyl ester
• CAS NO: 144978-12-1
• Molecular Formula: C₁₂H₁₉NO₅
• Molecular Weight: 257.28296
• Product Categories: pharmacetical;Pyroglutamic acid [Pyr, pGu]
• Mol File: 144978-12-1.mol

Chemical Properties

• Melting Point: 52.0 to 56.0 °C
• Boiling Point: 375 °C at 760 mmHg
• Flash Point: 180.6 °C
• Appearance: White crystalline powder
• Density: 1.182 g/cm³
• Vapor Pressure: 8.03E-06mmHg at 25°C
• Refractive Index: 1.486
• Storage Temp.: Keep in dark place,Sealed in dry,Room Temperature
• Solubility: soluble in Methanol
• PKA: -4.15±0.40(Predicted)
• CAS DataBase Reference: BOC-PYR-OET(CAS DataBase Reference)
• NIST Chemistry Reference: BOC-PYR-OET(144978-12-1)
• EPA Substance Registry System: BOC-PYR-OET(144978-12-1)

Safety Data

• Hazardous Substances Data: 144978-12-1(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
BOC-PYR-OET is used as a key intermediate in the synthesis of various pharmaceutical compounds for the development of new drugs and therapies.
Used in Synthesis of HCV Protease Inhibitors:
BOC-PYR-OET is used as a building block in the synthesis of Hepatitis C Virus (HCV) protease inhibitors. These inhibitors are essential for the development of antiviral drugs that target and inhibit the replication of the HCV, thus helping to treat Hepatitis C.
Used in Synthesis of Alkyl Renin Inhibitors:
BOC-PYR-OET is also used in the synthesis of alkyl renin inhibitors, which are important for the development of antihypertensive drugs. These inhibitors help regulate the renin-angiotensin system, playing a vital role in controlling high blood pressure and managing hypertension-related complications.

InChI:InChI=1/C12H19NO5/c1-5-17-10(15)8-6-7-9(14)13(8)11(16)18-12(2,3)4/h8H,5-7H2,1-4H3/t8-/m0/s1

Upstream product

• 24424-99-5 di-tert-butyl dicarbonate 
• 7149-65-7 ethyl (S)-pyroglutamate 
• 98-79-3 L-Pyroglutamic acid 
• 1538-75-6 2,2-dimethylpropanoic anhydride 
• 68766-96-1 ethyl (R)-2-pyrrolidone-5-carboxylate 
• 122-51-0 orthoformic acid triethyl ester 
• 4042-36-8 D-pyrrolidone-5-carboxylic acid 
• 64-17-5 ethanol 
• 86938-17-2 2-(S)-tert-butoxycarbonylaminopentanedioic acid 1-ethyl ester 
• 52454-78-1 L-glutamic acid α-ethyl ester 
• 1118-89-4 diethyl-L-glutamate hydrochloride 
• 24608-52-4 tert-butyl chloroformate 

Downstream Products

• 144978-17-6 (S)-2-tert-Butoxycarbonylamino-6-(diethoxy-phosphoryl)-5-oxo-hexanoic acid ethyl ester 
• 153080-85-4 ethyl (2S,4R)-1-(tert-butoxycarbonyl)-4-benzylpyroglutamate 
• 151957-52-7 (S)-2-tert-Butoxycarbonylamino-5-oxo-6-((R)-toluene-4-sulfinyl)-hexanoic acid ethyl ester 
• 153783-18-7 Ethyl (S)-2-(tert-butoxycarbonylamino)-5-phenyl-5-oxopentanoate 
• 153080-86-5 ethyl (2S,4R)-1-(tert-butoxycarbonyl)-4-p-tolylmethylpyroglutamate 
• 153783-19-8 (S)-2-tert-Butoxycarbonylamino-5-(4-chloro-phenyl)-5-oxo-pentanoic acid ethyl ester 
• 194594-23-5 5-hydroxy-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-ethyl ester 
• 153080-81-0 (2S,4R)-1-tert-butyl 4-allyl-2-ethoxycarbonyl-5-oxopyrrolidine-1-carboxylate 
• 144978-32-5 (Z)-(R)-2-tert-Butoxycarbonylamino-7-hydroxy-5-oxo-7-phenyl-hept-6-enoic acid ethyl ester 
• 144978-13-2 (Z)-(S)-2-tert-Butoxycarbonylamino-7-hydroxy-5-oxo-7-phenyl-hept-6-enoic acid ethyl ester 
• 153783-21-2 Ethyl (S)-2-(tert-butoxycarbonylamino)-5-oxo-5-(p-tolyl)pentanoate 

Relevant articles and documents

C-glycosylation of cyclic N-acyliminium ions with trimethylsilyloxyfuran

C-glycosylation of 2-methoxy-5-alkoxycarbonyl pyrrolidines with trimethylsilyloxyfuran allows us to obtain the corresponding pyrrolidines contigus to a α,β-unsaturated butyrolactone.

Stereoselective construction of a key hydroindole precursor of epidithiodiketopiperazine (ETP) natural products

An asymmetric synthetic strategy for constructing the divergent-synthesis monomer of epidithiodiketopiperazine (ETP) natural products has been successfully developed. The functionalized 2,3,3a,4,7,7a-hexahydroindole scaffold was constructed by a diastereoselective inverse electron-demand Diels-Alder (IEDDA) reaction. This journal is the Partner Organisations 2014.

INHIBITORS OF NOROVIRUS AND CORONAVIRUS REPLICATION

Compounds of Formula (I) and methods of inhibiting the replication of viruses in a biological sample or patient, of reducing the amount of viruses in a biological sample or patient, and of treating a virus infection in a patient, comprising administering to said biological sample or patient an effective amount of a compound represented by Formula (I), a compound of Table A or B or a pharmaceutically acceptable salt thereof.

Preparation method of (s)-1-(t-butyloxycarboryl)-5-oxopyrrolidine-2-carboxylic acid ethyl ester

The invention discloses a preparation method of (s)-1-(t-butyloxycarboryl)-5-oxopyrrolidine-2-carboxylic acid ethyl ester and aims at mainly solving the technical problems of complexity, long period,high cost, low yield and the like in the original technology. In the technical scheme of the invention, the preparation method comprises the following steps of step 1, preparation of boc-glu-oet: mixing h-glu-oet with a protective agent of boc- groups to prepare the boc-glu-oet, or mixing boc-glu-oh with ethyl acetate, performing reaction on a mixture under the action of diazoalkane, and performing treatment to obtain the boc-glu-oet; step 2, preparation of carboxyl active ester of the boc-glu-oet: mixing the boc-glu-oet with a carboxyl activating reagent, and performing low-temperature reaction on a mixture under the action of condensing agent to prepare a carboxyl activator of the boc-glu-oet; and sep 3, preparation of boc-pyr-oet: performing intramolecular cyclization on the carboxyl activator of the boc-glu-oet to prepare a crude product, and then performing extraction, purification and crystallization to obtain a target product. The preparation method provided by the invention greatly simplifies the process route, lowers the cost and is suitable for mass production.

Green preparation method of N-substituted-L-pyroglutamate

The invention provides a green preparation method of N-substituted-L-pyroglutamate. The method comprises the steps as follows: L-glutamic acid diester hydrochloride (III) is prepared from L-glutamic acid (II) as a starting material in the presence of an acidic reagent by an esterification reaction; then, L-glutamic acid diester hydrochloride (III) is subjected to N-substituted protective reactionwith an N-substituent protective reagent with a one-pot method in the presence of a base and a solvent, an N-substituted protective group is introduced, heating is performed for dealcoholization cyclization in molecules, and N-substituted-L-pyroglutamate as shown in the formula (I) is obtained. The method has the advantages of cheap and easily available raw materials, classic reaction types, shortprocess route, simple and convenient operation, small waste water amount, green and environment-friendly production process, high reaction yield and low product cost. 5R-benzyloxyaminopiperidine-2S-carboxylate, 5R-benzyloxyaminopiperidine-2S-formate ethanedioate and avibactam can be prepared from N-substituted-L-pyroglutamate as shown in the formula (I).

POLYMYXIN ANALOGS USEFUL AS ANTIBIOTIC POTENTIATORS

The disclosure provides compounds of the formula (I) or a tautomer thereof, or a pharmaceutically acceptable salt of either of the foregoing. The variables A, R1, and R2 are defined in the disclosure. The disclosure further includes pharmaceutical compositions comprising a compound of formula I together with at least one pharmaceutically acceptable carrier. The disclosure also includes a method of sensitizing bacteria to an antibacterial agent, comprising administering to a patient infected with the bacteria, simultaneously or sequentially, a therapeutically effective amount of the antibacterial agent and a compound of formula (I).

PROCESS FOR PREPARING DIPEPTIDYL PEPTIDASE IV INHIBITORS AND INTERMEDIATES THEREFOR

A process for preparing an amine of the structure which comprises a. treating an aqueous solution of a keto acid of the structure with ammonium formate, nicotinamide adenine dinucleotide, dithiothreitol and partially purified phenylalanine dehydrogenase and/or formate dehydrogenase enzyme (PDH/FDH); and b. adjusting pH of the reaction mixture with sodium hydroxide to form the desired amine which is substantially free of undesirable excess ammonium ions.

Proline compounds as Granzyme B inhibitors

Proline compounds as Granzyme B inhibitors, compositions that include the compounds, and methods for using the compounds. Methods for treating cutaneous scleroderma, epidermolysis bullosa, radiation dermatitis, alopecia areata, and discoid lupus erythematosus are provided.

SPIRO COMPOUNDS AS HEPATITIS C VIRUS INHIBITORS

Disclosed are spiro compounds of formula (I), or stereomers, geometric isomers, tautomers, nitrogen oxides, hydrates, solvates, metabolites, pharmaceutically acceptable salts or prodrugs thereof. The compounds can be used to treat hepatitis C virus (HCV) infection or hepatitis C disease. Furthermore disclosed are pharmaceutical compositions containing the compounds and the method of using the compounds or pharmaceutical compositions in the treatment of HCV infection or hepatitis C disease.

CYCLIC AMINE DERIVATIVES AS EP4 RECEPTOR ANTAGONISTS

There is described a novel group of cyclic amine derivative compounds, having an EP4 receptor antagonistic activity and specifically pharmaceutical compounds which are useful for the treatment or alleviation of Prostaglandin E mediated diseases. The present invention therefore relates to novel compounds which are selective antagonists of the EP4 subtype of PGE2 receptors with analgesic and antinflammatory activity, processes for their preparation, pharmaceutical compositions containing them and their use as medicaments, inter alia for the treatment or alleviation of Prostaglandin E mediated diseases such as acute and chronic pain, osteoarthritis, inflammation-associated disorder as arthritis, rheumatoid arthritis, cancer, migraine and endometriosis.