Substituted cyslopentane and cyclopentene compounds useful as neuraminidase inhibitors
A compound and alkyl technology, applied in the field of substituted cyclopentane and cyclopentene compounds used as neuraminidase inhibitors, can solve the problem of no disclosure of cyclopentane and cyclopentene derivatives, etc.
- Summary
- Abstract
- Description
- Claims
- Application Information
AI Technical Summary
Problems solved by technology
Method used
Examples
Embodiment 1
[0133] Embodiment 1 (±) 4-azidocyclopent-2-en-1-one (2, scheme 1)
[0134] Under stirring, 4-bromocyclopent-2-en 1-one (1, 3.5 g, 21.7 mmol) was added dropwise to a solution of sodium azide (2.12 g, 32.6 mmol) in DMF (15 ml) cooled at 0 , prepared by the method of Depuy et al. J. Org. Chem. 29, 3503, 1964) in DMF (5 ml) for 5 minutes. The reaction mixture was stirred at 0°C for 30 minutes and diluted with ethyl acetate (20ml). The reaction mixture was washed with water (2×20ml) and brine (2×20ml), dried (MgSO 4 ),filter. The filtrate was concentrated in vacuo to give an oily residue. Purification by flash column chromatography (silica gel, 10-15% ethyl acetate in hexanes) afforded 1.9 g (71%) of compound 2 as an oil.
[0135] 1 H NMR (CDCl 3 ): δ2.35(dd, J=18.6 and 2.4Hz, 1H), 2.77(dd, J=18.6 and 6.6Hz, 1H), 4.67(dd, J=4.9 and 2.6Hz, 1H), 6.35(dd, J=5.6 and 1.5Hz, 1H), 7.54 (dd, J=5.5 and 2.4Hz, 1H).
Embodiment 2
[0136] Example 2 (±) 3β-[1'-acetylamino-1'-bis(ethoxycarbonyl)]methyl-4α-azidocyclopent-1-one (3, scheme 1)
[0137] To a solution of diethyl acetamidomalonate (1.25 g, 5.7 mmol) in ethanol (10 mL) was added freshly chopped sodium metal (0.03 g, 1.4 mmol) under nitrogen. The reaction solution was stirred at room temperature until all the sodium metal was dissolved. The reaction mixture was cooled to -40°C, and a solution of compound 2 (0.7 g, 5.7 mmol) in ethanol (5 ml) was added dropwise. The reaction mixture was stirred at -40°C for 30 minutes and quenched with trifluoroacetic acid (0.1 ml, 1.4 mmol). The solvent was removed in vacuo to afford crude compound 3 as a white solid. The solid was dissolved in ethyl acetate, washed with water, dried and concentrated in vacuo. The resulting solid was crystallized from ether / hexane to afford 1.29 (63%) of compound 3 as a white solid, mp 121-122°C.
[0138] 1 H NMR (CDCl 3 ): δ1.26(t, J=7.2 Hz, 3H), 1.29(t, J=7.2Hz, 3H), 2.05(...
Embodiment 3
[0139] Example 3 (±)3 β-[1'-Acetamido-1'-bis(ethoxycarbonyl)]methyl-4α-tert-butoxycarbonylaminocyclopent-1-one (4, scheme 1)
[0140] A mixture of compound 3 (0.5 g, 1.5 mmol), di-tert-butyl dicarbonate (0.39 g, 1 / 77 mmol) and 10% Pd / C (0.14 g) in ethyl acetate (25 ml) was hydrogenated at 45 psi 1 hour. The catalyst was filtered off, and the filtrate was concentrated in vacuo to afford crude compound 4. Recrystallization from ether / hexane gave 0.28 g (45%) of compound 4 as a white solid, mp 135-136°C.
[0141] 1 H NMR (CDCl 3 ): δ1.27(m, 6H), 1.45(s, 9H), 2.10(s, 3H), 2.33(m, 2H), 2.75(m, 2H), 3.25(m, 1H), 4.14(m, 1H), 4.28(m, 4H), 4.83(s, 1H), 6.98(s, 1H); IR(KBr) 3365, 2980, 1739, 1689, 1519, 1394, 1275cm -1 : mS (CI-): 413 (10%, M-1). Elemental Analysis: Calculated Values (C 19 h 30 N 2 o 8 ): C, 55.06; H, 7.30; N, 6.76 Found: C, 54.63; H, 7.17; N, 6.74
PUM
| Property | Measurement | Unit |
|---|---|---|
| melting point | aaaaa | aaaaa |
| melting point | aaaaa | aaaaa |
| melting point | aaaaa | aaaaa |
Abstract
Description
Claims
Application Information
Login to view more - R&D Engineer
- R&D Manager
- IP Professional
- Industry Leading Data Capabilities
- Powerful AI technology
- Patent DNA Extraction
Browse by: Latest US Patents, China's latest patents, Technical Efficacy Thesaurus, Application Domain, Technology Topic.
© 2024 PatSnap. All rights reserved.Legal|Privacy policy|Modern Slavery Act Transparency Statement|Sitemap