Preparation method for moxifloxacin intermediate (1S, 6R)-8-benzyl-7, 9-dioxy-2, 8-diazabicyclo [4.3.0] nonane
A technology of diazabicyclo and moxifloxacin, which is applied in organic chemistry methods, chemical instruments and methods, organic racemization, etc., can solve the problems of inconvenient large-scale production, high optical purity, and low content, and achieve the reduction of raw material consumption, Effect of avoiding purification process and reducing production cost
- Summary
- Abstract
- Description
- Claims
- Application Information
AI Technical Summary
Problems solved by technology
Method used
Image
Examples
Example Embodiment
[0051] Example 1
[0052] 10.00g (40.94mmol) cis-8-benzyl-7,9-dioxo-2,8-diazabicyclo[4.3.0]nonane in a 250ml reaction flask, add 100ml isopropyl acetate, room temperature Stir until all of it is dissolved, add 4.25g (24.54mmol) N-acetyl-L-leucine, heat up to 70-80℃ and react for 40 minutes, slowly reduce the temperature to 40℃, and crystals will precipitate, continue to cool down to 25℃, stir overnight. The next day, filter, wash the reaction flask with the filtrate, and wash the crystals with 4g×2 isopropyl acetate to obtain (1 S ,6 R )-8-benzyl-7,9-dioxo-2,8-diazabicyclo[4.3.0]nonane·N-acetyl-L-leucine salt, wet weight 7.80g, reduced pressure at 40°C Dry, weighs 7.75g, theoretical yield is 90.69%, optical purity is 95.05% ee.
[0053] The 7.75g obtained above (1 S ,6 R )-8-benzyl-7,9-dioxo-2,8-diazabicyclo[4.3.0]nonane·N-acetyl-L-leucine salt, recrystallized with 44g of acetonitrile, the obtained crystals are 40 Drying under reduced pressure at ℃ weighs 6.31g, the total yield ...
Example Embodiment
[0055] Example 2
[0056] (1 S ,6 R )-8-benzyl-7,9-dioxo-2,8-diazabicyclo[4.3.0]nonane·N-acetyl-L-leucine salt 6.31g (15.11mmol) floating 15g To the methyl chloride, add 16g water and 1.5g NaHCO 3 , Stir at 31°C, after the two phases are clear, separate the organic phase, and extract the aqueous phase with 5g×2 dichloromethane. The organic phases were combined, dried with 5 g of anhydrous sodium sulfate, filtered, washed with 5 g of dichloromethane, and the obtained filtrate was recovered under reduced pressure to recover dichloromethane to obtain the product (1 S ,6 R )-8-benzyl-7,9-dioxo-2,8-diazabicyclo[4.3.0]nonane 3.44g, [α] D 20 = -24.4?? (c=0.005, ethanol), the optical purity is 99.31%ee.
[0057] 1 HNMR (CDCl 3 , MHz) δppm: 7.23-7.34 (m, 5H), 4.62 (s, 2H), 3.79-3.81 (d, 1H), 2.79-2.85 (dd, 1H), 2.73-2.78 (m,1H), 2.61- 2.67 (m, 1H), 2.16 (br s, 1H), 1.89-1.97 (m, 1H), 1.59-1.68 (m, 1H), 1.45-1.51 (m, 2H).
[0058] 13 CNMR (CDCl 3 , MHz) δppm: 177.92, 177.76, 135.83, 128.61,...
Example Embodiment
[0059] Example 3
[0060] Method 46 Preparation (1 S ,6 R )-8-benzyl-7,9-dioxo-2,8-diazabicyclo[4.3.0]nonane·N-acetyl-L-leucine salt 7.27g (17.41mmol) suspended in 15g toluene Medium, add 16g water and 1.6g NaHCO 3 , Stir at 30°C, after the two phases are clear, separate the organic phase, and extract the water phase with 5g×2 toluene. The organic phases were combined, dried with 5 g of anhydrous sodium sulfate, filtered, and washed with 4.5 g of toluene. The obtained filtrate was decompressed to recover toluene to obtain the product (1 S ,6 R )-8-benzyl-7,9-dioxo-2,8-diazabicyclo[4.3.0]nonane 4.26g, optical purity: 92.63%ee.
PUM
Property | Measurement | Unit |
Optical purity | aaaaa | aaaaa |
Abstract
Description
Claims
Application Information

- 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.
© 2023 PatSnap. All rights reserved.Legal|Privacy policy|Modern Slavery Act Transparency Statement|Sitemap