103201-79-2

Basic information

• Product Name: (+)-(3R,7aS)-Tetrahydro-3-phenyl-3H,5H-pyrrolo1,2-coxaole-5-one
• Synonyms: (3R,7aS)-3-Phenyl-tetrahydro-pyrrolo[1,2-c]oxazol-5-one;(+)-(3R,7αS)-Tetrahydro-3-phenyl-3H,5H-pyrrolo1,2-coxaole-5-one;(+)-(3R,7aS)-Tetrahydro-3-phenyl-3H,5H-pyrrolo[1,2-c]oxazol-5-one;(3R,7aS)-Tetrahydro-3-phenyl-3H,5H-pyrrolo[1,2-c]oxazol-5-one;3H,5H-Pyrrolo[1,2-c]oxazol-5-one, tetrahydro-3-phenyl-, (3R,7aS)-;(3R,7aS)-3-phenyltetrahydropyrrolo[1,2-c]oxazol-5(1H)-one;(3R,7aS)-3-Phenyltetrahydropyrrolo[1,2-c]oxazol-5(3H)-one;(3R,7aS)-3-phenyltetrahydro-3H,5H-pyrrolo[1,2-c]oxazol-5-one
• CAS NO: 103201-79-2
• Molecular Formula: C₁₂H₁₃NO₂
• Molecular Weight: 203.2371
• Product Categories: pharmacetical;Heterocyclic Building Blocks
• Mol File: 103201-79-2.mol
• Article Data: 28

Chemical Properties

• Melting Point: <25 °C
• Boiling Point: 383.2 °C at 760 mmHg
• Flash Point: 185.6 °C
• Appearance: /
• Density: 1.25 g/cm³
• Vapor Pressure: 4.47E-06mmHg at 25°C
• Refractive Index: 1.608
• Storage Temp.: 2-8°C
• Solubility: Chloroform (Sparingly), Ethyl Acetate (Slightly)
• PKA: -1.61±0.40(Predicted)
• CAS DataBase Reference: (+)-(3R,7aS)-Tetrahydro-3-phenyl-3H,5H-pyrrolo1,2-coxaole-5-one(CAS DataBase Reference)
• NIST Chemistry Reference: (+)-(3R,7aS)-Tetrahydro-3-phenyl-3H,5H-pyrrolo1,2-coxaole-5-one(103201-79-2)
• EPA Substance Registry System: (+)-(3R,7aS)-Tetrahydro-3-phenyl-3H,5H-pyrrolo1,2-coxaole-5-one(103201-79-2)

Safety Data

• Hazardous Substances Data: 103201-79-2(Hazardous Substances Data)

Usage

Description

(+)-(3R,7aS)-Tetrahydro-3-phenyl-3H,5H-pyrrolo1,2-coxaole-5-one is a complex organic compound characterized by its unique molecular structure and chiral properties. It is a viscous oil, which indicates its high molecular weight and potential for use in various chemical and pharmaceutical applications.

Uses

Used in Pharmaceutical Industry:
(+)-(3R,7aS)-Tetrahydro-3-phenyl-3H,5H-pyrrolo1,2-coxaole-5-one is used as a key intermediate in the synthesis of Boceprevir (B674500) and its analogs. Boceprevir is a hepatitis C virus (HCV) protease inhibitor, which plays a crucial role in the treatment of chronic hepatitis C infection. (+)-(3R,7aS)-Tetrahydro-3-phenyl-3H,5H-pyrrolo1,2-coxaole-5-one's unique structure and chirality are essential for the development of these therapeutic agents, as they contribute to the drug's efficacy and selectivity in targeting the viral protease enzyme.

InChI:InChI=1/C12H13NO2/c14-11-7-6-10-8-15-12(13(10)11)9-4-2-1-3-5-9/h1-5,10,12H,6-8H2/t10-,12+/m0/s1

Upstream product

• 100-52-7 benzaldehyde 
• 62400-75-3 pyroglutamol 
• 98-79-3 L-Pyroglutamic acid 
• 17342-08-4 (S)-Pyroglutaminol 
• 4931-66-2 methyl (S)-pyroglutamate 
• 6525-53-7 L-glutamic acid dimethyl ester 
• 104-15-4 toluene-4-sulfonic acid 
• 7149-65-7 ethyl (S)-pyroglutamate 
• 74936-93-9 (S)-5-oxopyrrolidine-2-carbonyl chloride 
• 56-86-0 L-glutamic acid 

Downstream Products

• 134107-65-6 (3R,7aS)-3-phenyl-3,7a-dihydro-1H-pyrrolo[1,2-c]oxazol-5-one 
• 134107-63-4 (+)-(2R,5S,7S)-1-aza-3-oxa-2-phenyl-7-(phenylselenenyl)bicyclo<3.3.0>octan-8-one 
• 134037-88-0 (+)-(2R,5S,7R)-1-aza-3-oxa-2-phenyl-7-(phenylmethyl)bicyclo<3.3.0>octan-8-one 
• 134107-62-3 (+)-(2R,5S,7S)-1-aza-3-oxa-2-phenyl-7-(phenylmethyl)bicyclo<3.3.0>octan-8-one 
• 134037-91-5 (2R,5S)-1-aza-3-oxa-2-phenyl-7-(4'-nitrophenyl(hydroxy)methyl)bicyclo<3.3.0>octan-8-one 
• 108827-55-0 (4S,6aR,10R,12aS)-4,10-Diphenyl-octahydro-5,11-dioxa-3a,9a-diaza-dicyclopenta[a,f]cyclodecene-3,9-dione 
• 134037-92-6 (3R,7aS)-6-(Hydroxy-phenyl-methyl)-3-phenyl-tetrahydro-pyrrolo[1,2-c]oxazol-5-one 
• 138231-10-4 (+)-(2R,5S,7R)-1-aza-3-oxa-2-phenyl-7-allylbicyclo<3.3.0>octan-8-one 
• 138078-57-6 (+)-(2R,5S,7S)-1-aza-3-oxa-2-phenyl-7-allylbicyclo<3.3.0>octan-8-one 
• 138231-09-1 (+)-(2R,5S,7R)-1-aza-3-oxa-2-phenyl-7-(4'-nitrophenylmethyl)bicyclo<3.3.0>octan-8-one 
• 138078-56-5 (+)-(2R,5S,7S)-1-aza-3-oxa-2-phenyl-7-(4'-nitrophenylmethyl)bicyclo<3.3.0>octan-8-one 
• 254909-27-8 (2R,5S)-7-ethoxycarbonyl-2-phenyl-1-aza-3-oxa-lbicyclo<3.3.0>octan-8-one 
• 878722-66-8 (2R,5S,7R,1'S)-1-aza-7-(1'-cyano-1'-phenylmethyl)-7-(ethoxycarbonyl)-3-oxo-8-oxa-2-phenylbicyclo[3.3.0]octane 
• 1340543-05-6 (2R,5S,7R)-1-aza-7-(4-amino-2-nitrophenyl)-7-(ethoxycarbonyl)-3-oxo-8-oxa-2-phenylbicyclo[3.3.0]octane 

Relevant articles and documents

Highly diastereoselective alkylation of a pyroglutamate derivative with an electrophile obtained from indole. Synthesis of a potential intermediate for the preparation of the natural sweetener (-)-Monatin

The synthesis of a potential intermediate for the preparation of the very intensive sweetening agent (-)-Monatin is described. The synthesis is based on a highly diastereoselective alkylation reaction of a pyroglutamate derivative with an electrophile obtained from indole.

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