200002-41-1

Basic information

• Product Name: 2-Azabicyclo[2.2.1]hept-5-ene-2-carboxylic acid, 3-oxo-,1,1-dimethylethyl ester, (1S,4R)-
• Synonyms: Tert-butyl (1R,4S)-3-oxo-2-azabicyclo[2.2.1]hept-5-ene-2-carboxylate
• CAS NO: 200002-41-1
• Molecular Formula: C₁₁H₁₅NO₃
• Molecular Weight: 209.2417
• Mol File: 200002-41-1.mol

Chemical Properties

• CAS DataBase Reference: 2-Azabicyclo[2.2.1]hept-5-ene-2-carboxylic acid, 3-oxo-,1,1-dimethylethyl ester, (1S,4R)-(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Azabicyclo[2.2.1]hept-5-ene-2-carboxylic acid, 3-oxo-,1,1-dimethylethyl ester, (1S,4R)-(200002-41-1)
• EPA Substance Registry System: 2-Azabicyclo[2.2.1]hept-5-ene-2-carboxylic acid, 3-oxo-,1,1-dimethylethyl ester, (1S,4R)-(200002-41-1)

Safety Data

• Hazardous Substances Data: 200002-41-1(Hazardous Substances Data)

Usage

Property

Tert-butyl ester of a bicyclic beta-lactam compound

Upstream product

• 130931-83-8 (1S,4R)-2-azabicyclo[2,2,1]hept-5-en-3-one 
• 24424-99-5 di-tert-butyl dicarbonate 
• 162427-15-8 3-oxo-2-aza-bicyclo[2.2.1]hept-5-ene-2-carboxylic acid tert-butyl ester 

Downstream Products

• 130931-85-0 (+)-(1R,4S)-4-aminocyclopent-2-ene-1-carboxylic acid hydrochloride 
• 1007125-08-7 (-)-(1R,2S,3R,5R)-3-((tert-butoxycarbonyl)amino)-5-(hydroxymethyl)cyclopentane-1,2-diyl dibenzoate 
• 1007125-09-8 (-)-(1R,2S,3R,5R)-3-amino-5-(hydroxymethyl)cyclopentane-1,2-diyl dibenzoate hydrochloride 
• 1450975-28-6 (+)-(1R,2S,5R)-5-(hydroxymethyl)cyclopent-3-ene-1,2-diyl dibenzoate 
• 347185-68-6 tert-butyl ((1R,3S)-3-(hydroxymethyl)cyclopentyl)carbamate 
• 1007125-06-5 (-)-(1R,4S,5R,6S)-tert-butyl 5,6-dihydroxy-3-oxo-2-azabicyclo[2.2.1]heptane-2-carboxylate 
• 1203306-05-1 (1R,3R)-3-aminocyclopentane-1-carboxylic acid hydrochloride 
• 1400583-12-1 cis-methyl 3-((tert-butoxycarbonyl)amino)cyclopentane-1-carboxylate 
• 1400583-12-1 trans-methyl 3-((tert-butoxycarbonyl)amino)cyclopentane-1-carboxylate 
• 489446-85-7 (1R,3R)-3-((tert-butoxycarbonyl)amino)cyclopentane-1-carboxylic acid 
• 489446-72-2 (1R,3R)-3-tert-butoxycarbonylaminocyclopentanecarboxylic acid methyl ester 
• 108999-93-5 (1S,4S)-N-tert-butoxycarbonyl-4-aminocyclopent-2-ene-1-carboxylic acid 
• 1312161-66-2 C₁₁H₁₇NO₄ 
• 151907-80-1 (1R,4S)-4-[(tert-butoxycarbonyl)amino]cyclopent-2-ene-1-carboxylic acid 

Relevant articles and documents

Regio- and Stereoselective Ring-Opening Metathesis Polymerization of Enantiomerically Pure Vince Lactam

The ring-opening metathesis polymerization (ROMP) of (+)-Vince lactam [(S)-azabicyclo[2.2.1]hept-5-en-3-one] (1) and its N-benzyl, N-trimethylsilyl (TMS), and N-tert-butoxycarbonyl (Boc) derivatives (2a-c) is reported. Highly cis-syndiotactic (st) poly(Vince lactam) was readily accessible by using the cyclometalated ruthenium complex Ru[CH(2-OiPr-Ph)](Piv)(1-mesityl-3-C4H8-imidazol-2-ylidene) (Piv =2,2-dimethylpropanoate) (4); however, small amounts of trans double bonds (ca. 5%) formed. Highly cis-st (>98%) polymers were accessible by the action of the monoaryloxide pyrrolide (MAP) type complexes W(N-2,6-iPr2C6H3)(CHCMe2Ph)(Pyr)(HMTO) (Pyr = pyrrolide, HMTO = 2,6-(2,4,6-Me3C6H2)2C6H3O) (7) and W(O)(CHCMe2Ph)(PMe2Ph)(Me2Pyr)(TPPO) (TPPO = 2,3,5,6-tetraphenylphenolate) (8). Complementary, cis-isotactic (>98% cis-it) polymers were prepared by the action of Mo(N-2,6-Me2C6H3)(CHCMe2Ph)(OBiphen) (OBiphen = 3,3′-di-tert-butyl-5,5′,6,6′-tetramethyl-1,1′-biphenyl-2,2′-diolate) (5) and its tungsten analogue W(N-2,6-Me2C6H3)(CHCMe2Ph)(OBiphen) (6). Notably, none of these Mo- and W-based initiators polymerize unprotected Vince lactam. Deprotection of poly(N-TMS Vince lactam) and poly(N-Boc Vince lactam) with neat trifluoroacetic acid allowed for the isolation of all-cis highly tactic poly(Vince lactam).

PYRAZOLO-PYRIMIDIN-AMINO-CYCLOALKYL COMPOUNDS AND THEIR THERAPEUTIC USES

Disclosed herein are pyrazolo-pyrimid in-ami no-cycloalkyl compounds, analogs thereof, pharmaceutical compositions comprising thereof and therapeutic uses therefor.

3-CARBON SUBSTITUTED 4-AMINOCYCLOPENT-1-ENE-1-CARBOXYLIC ACID COMPOUNDS AS INHIBITORS OF GAMMA-AMINOBUTYRIC ACID (GABA) AMINOTRANSFERASE

Disclosed are cyclopentene compounds for use as inhibitors of gamma-aminobutyric acid (GABA) aminotransferase (AT) and/or ornithine aminotransferase (OAT). The disclosed cyclopentene compounds include 3-carbon substituted 4-aminocyclopent-1-ene-carboxylic acid compounds which may be formulated in pharmaceutical composition for treating diseases and disorders associated with GABA-AT and/or OAT activity, including epilepsy, addiction, and hepatocellular carcinoma (HCC).

A Mitsunobu reaction to functionalized cyclic and bicyclic N-arylamines

The scope of an unexpected Mitsunobu cyclisation to prepare N-arylated Fsp3-enriched azacycles was investigated. In the current study, we have identified whether a pKa-dependent Mitsunobu cyclodehydration or a pKa-independent Mitsunobu intramolecular reaction was in operation. A Mitsunobu reaction, creating a leaving group, followed by intramolecular nucleophilic displacement was determined to be the dominant pathway.

SPIRO [2.4]HEPTANES FOR TREATMENT OF FLAVIVIRIDAE INFECTIONS

Compounds, methods, and compositions for the treatment of infections in or exposure to humans and other host animals of Flaviviridae viruses, including HCV, that includes the administration of an effective amount of a spiro[2.4]heptane as described herein

Synthesis of highly functionalized cyclopentanes as precursors of hydroxylated azidocarbonucleosides

Regio- and stereoisomers of functionalized azido amino alcohols with a cyclopentane skeleton were synthesized in enantiomerically pure forms. Enzymatic ring cleavage of racemic2-azabicyclo[2.2.1]hept-5-en-3-one gave the corresponding amino acid and one enantiomer of the lactam stereospecifically. These were protected by esterification and carbamoylation, and then epoxidized. The resulting oxiranes underwent cleavage by sodium azide with complementary stereoselectivities. The regioisomeric products were easily separated by crystallization or column chromatography.

Enzymatic method for the synthesis of blockbuster drug intermediates - Synthesis of five-membered cyclic γ-amino acid and γ-lactam enantiomers

A very efficient enzymatic method was developed for the synthesis of cyclic γ-lactam and γ-amino acid enantiomers, intermediates for drugs with a prominent turnover (e.g., abacavir and carbovir), through the CAL-B-catalysed enantioselective (E > 200) hydrolysis of the corresponding N-Boc protected and unprotected racemic γ-lactams with H2O in iPr2O. Wiley-VCH Verlag GmbH & Co. KGaA, 2008.

DIPEPTIDYL PEPTIDASE IV INHIBITOR COMPOUNDS AND COMPOSITIONS

The present invention relates to dipeptidyl peptidase IV (DPP-IV) inhibitors of formula (1), pharmaceutical compositions containing them, processes for their preparation, and methods for treating disorders mediated by DPP-IV inhibition, such as diabetes, especially Type II diabetes, with them, wherein Rj is substituted or unsubstituted alkyl, substituted or unsubstituted alkenyl, substituted or unsubstituted alkynyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted cycloalkylalkyyl, substituted or unsubstituted aryl, substituted or unsubstituted arylalkyl, substituted or unsubstituted heteroaryl, substituted or unsubstituted heteroarylalkyl, substituted or unsubstituted heterocyclic ring, substituted or unsubstituted heterocyclylalkyl; R2 is hydrogen or Q-β alkyl; Y is -S(O)m, -CH2-, -CHF or CF2; R3 is hydrogen, nitrile (-CN), COOH, or an isostere of a carboxylic acid.

NOVEL DIPEPTIDYL PEPTIDASE IV INHIBITORS, PHARMACEUTICAL COMPOSITIONS CONTAINING THEM, AND PROCESS FOR THEIR PREPARATION

The present invention relates to novel compounds useful as dipeptidyl peptidase IV (DPP-IV) inhibitors of the formula: (I) wherein Y is -S(O)m, -CH2-, CHF, or -CF2; m is 0, 1, or 2; X is a bond, C1-C5 alkyl (e.g., -CH2-), or -C(=0)-; the dotted line [----] in the carbocyclic ring represents an optional double bond; R1 is substituted or unsubstituted cycloalkyl, substituted or unsubstituted cycloalkylalkyl, substituted or unsubstituted cycloalkenyl, substituted or unsubstituted aryl, substituted or unsubstituted arylalkyl, substituted or unsubstituted heteroaryl, substituted or unsubstituted heterocyclic ring, substituted or unsubstituted heterocyclylalkyl, substituted or unsubstituted heteroarylalkyl, CN, -COOR3, CONR3R4, -OR3, -NR3R4, or NR3COR3; R2 is hydrogen, cyano, COOH, or an isostere of a carboxylic acid (such as SO3H, CONOH, B(OH)2, PO3R3R4, SO2NR3R4, tetrazole, -COOR3, -CONR3R4, NR3COR4, or -COOCOR3).

NOVEL DIPEPTIDYL PEPTIDASE IV INHIBITORS; PROCESS FOR THEIR PREPARATION AND COMPOSITIONS CONTAINING THEM

The present invention relates to novel organic compounds, more particularly, novel Dipeptidyl peptidase IV (DPP-IV) inhibitors of general formula (I) wherein: Y is -S(O)m-, -CH2-, -CHF-, or -CF2; X and Z are independently -C(=O)-, -NR3-, - O- or -S(O)m-; each occurrence of m is independently 0, 1 or 2; a is 0, 1 or 2; b is 0, 1 or 2; the dotted line [----] in the carbocyclic ring represents an optional double bond; R1 is substituted or unsubstituted alkyl, substituted or unsubstituted alkenyl, substituted or unsubstituted alkynyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted cycloalkylalkyl, substituted or unsubstituted cycloalkenyl, substituted or unsubstituted aryl, substituted or unsubstituted arylalkyl, substituted or unsubstituted heteroaryl, substituted or unsubstituted heterocyclic ring, substituted or unsubstituted heterocyclylalkyl, or substituted or unsubstituted heteroarylalkyl; R2 is hydrogene, nitrile (-CN), COOH, or an isostere of carboxylic; or analogs, tautomers, enantiomers, diastereomers, regioisomers, stereoisomers, polymorphs, pharmaceutically acceptable salts, N-oxides, pharmaceutically acceptable solvates and pharmaceutical compositions containing them.