134107-65-6

Basic information

• Product Name: [S]-3-Phenyl-1,7a-dihydro-pyrrolo[1,2-c]oxazol-5-one
• Synonyms: [S]-3-Phenyl-1,7a-dihydro-pyrrolo[1,2-c]oxazol-5-one;(7aS)-3-Phenyl-1,7a-dihydropyrrolo[1,2-c]oxazol-5(3H)-one ;(3R,7aS)-1,7a-Dihydro-3-phenyl-3H,5H-pyrrolo[1,2-c]oxazol-5-one;3-Phenyl-1,7a-dihydropyrrolo[1,2-c]oxazol-5(3H)-one
• CAS NO: 134107-65-6
• Molecular Formula: C₁₂H₁₁NO₂
• Molecular Weight: 201.22124
• Product Categories: Chiral Reagents;Heterocycles;Intermediates & Fine Chemicals;Pharmaceuticals
• Mol File: 134107-65-6.mol

Chemical Properties

• Boiling Point: 424.6±45.0 °C(Predicted)
• Appearance: /
• Density: 1.29±0.1 g/cm3(Predicted)
• Storage Temp.: 2-8°C
• Solubility: Dichloromethane, Ether, Ethyl Acetate
• PKA: -2.06±0.40(Predicted)
• CAS DataBase Reference: [S]-3-Phenyl-1,7a-dihydro-pyrrolo[1,2-c]oxazol-5-one(CAS DataBase Reference)
• NIST Chemistry Reference: [S]-3-Phenyl-1,7a-dihydro-pyrrolo[1,2-c]oxazol-5-one(134107-65-6)
• EPA Substance Registry System: [S]-3-Phenyl-1,7a-dihydro-pyrrolo[1,2-c]oxazol-5-one(134107-65-6)

Safety Data

• Hazardous Substances Data: 134107-65-6(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
[S]-3-Phenyl-1,7a-dihydro-pyrrolo[1,2-c]oxazol-5-one is used as a key intermediate in the synthesis of Boceprevir (B674500) and its analogs for the treatment of hepatitis C virus (HCV) infections. Its chiral nature and unique structure play a crucial role in the development of these therapeutic agents, contributing to their efficacy and selectivity in targeting the viral protease enzyme.

Upstream product

• 34837-55-3 Phenylselenyl bromide 
• 103201-79-2 (3R,7aS)-3-phenyl-tetrahydro-pyrrolo[1,2-c]oxazol-5-one 
• 56-86-0 L-glutamic acid 
• 100-52-7 benzaldehyde 
• 74936-93-9 (S)-5-oxopyrrolidine-2-carbonyl chloride 
• 17342-08-4 (S)-Pyroglutaminol 

Downstream Products

• 134037-94-8 (+)-(2R,5S,6R,7S)-7-Benzyl-6-[bis(methoxycarbonyl)methyl]-8-oxo-2-phenyl-3-oxa-1-azabicyclo[3.3.0]octane 
• 154495-19-9 (1aS,1bR,4R,5aS)-4-Phenyl-tetrahydro-1,3-dioxa-4a-aza-cyclopropa[a]pentalen-5-one 
• 154631-82-0 (2R,5R,6R,7R)-6,7-epoxy-2-phenyl-3-oxa-1-aza-bicyclo<3.3.0>octane-8-one 
• 160823-80-3 (3aS,3bR,6R,7aR)-2-benzyl-1,2,3a,3b,4,7a-hexahydro-6-phenyl-3,5-dioxa-2,6a-diazacyclopentapentalen-7-one 
• 169478-04-0 (2R,5S,6S)-6-(N-benzyl-N-hydroxy)amino-2-phenyl-3-oxa-1-azabicyclo[3.3.0]octane-8-one 
• 199436-23-2 (2R,5R,6S)-6-N-benzylamino-2-phenyl-3-oxa-1-azabicyclo[3.3.0]octane-8-one 
• 195818-99-6 (2R,5S,6S,11R)-8,9-dimethyl-12-oxo-2-phenyl-1-aza-3-oxa-tricyclo[7.3.0^1,5.0^6,11]dodec-8-ene 
• 220622-90-2 (3R,5aR,6aS,6bS)-3-phenyltetrahydro-3H-cyclopropa[3,4]pyrrolo[1,2-c]oxazol-5(1H)-one 
• 219753-99-8 (1S,2S,4S,7R)-6-aza-3,3-dimethyl-8-oxa-7-phenyltricyclo<4.3.0.0>nonan-5-one 
• 190850-55-6 (3R)-5-tert-butyldimethylsiloxy-3-phenyl-1H-pyrrolo[1,2-c]oxazole 

Relevant articles and documents

BACTERIAL EFFLUX PUMP INHIBITORS

Disclosed herein are compounds of formula I: (formula I) and salts thereof. Also disclosed are compositions comprising compounds of formula I and methods using compounds of formula I.

ANTIMICROBIAL COMPOUNDS AND METHODS

The invention is directed to compounds that are active as antibacterial agents. The invention compounds are active against gram-positive and gram-negative bacteria and can be used to treat infections caused by gram-positive and gram-negative bacteria. Also disclosed are processes and intermediates for making the compounds.

BENZIMIDAZOLE-LINKED INDOLE COMPOUND ACTING AS NOVEL DIVALENT IAP ANTAGONIST

The present invention discloses a benzimidazole-linked indole compound acting as novel divalent IAP antagonist, specifically disclosing the compound shown in fomulas (I) or a pharmaceutically acceptable salt thereof.

A pharmaceutical preparation of intermediate

The invention discloses preparation methods of drug intermediates. The preparation method of a drug intermediate shown as formula 2-1 includes the following steps: reacting compound 2 with phenyl disulfide (PhSSPh) in a solvent under the action of an alka

Design, synthesis and biological evaluation of small molecules as potent glucosidase inhibitors

Abstract Herein we have reported design, synthesis and in vitro biological evaluation of a library of bicyclic lactams that led to the discovery of compounds 6 and 7 as a novel class of α-glucosidase inhibitors. They inhibited α-glucosidase (yeast origin)

Alternative route towards the convergent synthesis of a human purine nucleoside phosphorylase inhibitor-forodesine HCl

Forodesine HCl is being investigated as a potential target for the control of T-cell proliferation. Herein we present an alternative route for the synthesis of the target molecule with addition of lactam to the lithiated deazahypoxanthine (generated in situ). The lactam was synthesized in five steps starting from l-pyroglutamic acid.

Discovery of (1R,5S)-N-[3-amino-1-(cyclobutylmethyl)-2,3-dioxopropyl]-3- [2(S)-[[[(1,1-dimethylethyl)amino]carbonyl]amino]-3,3-dimethyl-1-oxobutyl]-6, 6-dimethyl-3-azabicyclo[3.1.0]hexan-2(S)-carboxamide (SCH 503034), a selective, potent, orally bioavailable hepatitis C virus NS3 protease inhibitor: A potential therapeutic agent for the treatment of hepatitis C infection

Hepatitis C virus (HCV) infection is the major cause of chronic liver disease, leading to cirrhosis and hepatocellular carcinoma, which affects more than 170 million people worldwide. Currently the only therapeutic regimens are subcutaneous interferon-α or polyethylene glycol (PEG)-interferon-α alone or in combination with oral ribavirin. Although combination therapy is reasonably successful with the majority of genotypes, its efficacy against the predominant genotype (genotype 1) is moderate at best, with only about 40% of the patients showing sustained virological response. Herein, the SAR leading to the discovery of 70 (SCH 503034), a novel, potent, selective, orally bioavailable NS3 protease inhibitor that has been advanced to clinical trials in human beings for the treatment of hepatitis C viral infections is described. X-ray structure of inhibitor 70 complexed with the NS3 protease and biological data are also discussed.

Stereoselective synthesis of protected (2S,3S)-N-methyl-5- hydroxyisoleucine, a component of halipeptins

The stereocontrolled synthesis of the protected (2S,3S)-N-methyl-5- hydroxyisoleucine, a component of halipeptins A and B with potent anti-inflammatory activity, has been achieved. The key steps include (i) installation of a double bond to bicyclic lactam

Cyclopropanation reactions of pyroglutamic acid-derived synthons with akylidene transfer reagents

The cyclopropanation of unsaturated lactams 1 and 3 derived from pyroglutamic acid with nucleophilic alkylidene transfer reagents is investigated. Good-to-modest yields of cyclopropanes were obtained with most sulfur ylides explored. Syn/anti selectivity was found to be dependent on the synthon as well as the sulfur ylide. This cyclopropanation methodology is used in the synthesis of arginine and glutamic acid analogues.

Total synthesis of (+)-calyculin A and (-)-calyculin B: Cyanotetraene construction, asymmetric synthesis of the C(26-37) oxazole, fragment assembly, and final elaboration

A convergent total synthesis leading to (+)-calyculin A and (-)-calyculin B (1 and 2), antipodes of the potent, highly selective and remarkably cell-permeable phosphatase inhibitors calyculins A and B, has been achieved. In the preceding paper we outlined the asymmetric synthesis of the C(9-25) spiroketal dipropionate subunit (+)-BC; herein we describe construction of the C(1-8) cyanotetraene, an asymmetric synthesis of the C(26-37) oxazole, fragment assembly and final elaboration to (+)-1 and (-)-2. Highlights of the synthesis include: application of a one-pot three-component Suzuki reaction for the construction of phosphonate A, a bifunctional triene precursor of the light sensitive C(1-8) cyanotetraene subunit, an asymmetric synthesis of the C(26-32) oxazole (-)-D, exploiting the Silks-Odom 77Se NMR protocol to assess enantiomeric purity, construction of the C(33-37) subtarget (-)-E in a highly stereocontrolled fashion via an acyliminium ion, and a concise, highly efficient sequence for fragment assembly and elaboration to (+)-calyculin A and (-)-calyculin B. The synthesis of (-)-2 also confirms the structure of calyculin B, previously based only on spectral comparison with calyculin A.