Beta-lactam compounds and methods of use thereof
A technology of compounds and lactam rings, applied in organic chemistry methods, chemical instruments and methods, biochemical equipment and methods, etc., can solve problems such as delayed treatment and time-consuming
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Embodiment 1
[0244] Example 1. (E)-7-((3-methoxy-4-((3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolane Preparation of -2-yl)allyl)oxy)benzyl)oxy)-3H-phenoxazin-3-one (6).
[0245] Overall synthesis scheme:
[0246]
[0247] step 1:
[0248]
[0249] To a round bottom flask was added propargyl alcohol (1.00 g, 17.8 mmol) and DCM (20 mL). Then add NEt at 0 °C 3 (3.34 mL, 35.7 mmol) and TESCl (4.50 mL, 26.7 mmol). The resulting reaction mixture was warmed to room temperature and stirred for 3.5 hours. When TLC indicated the reaction was complete, the reaction was quenched with water (10 mL). The mixture was partitioned with DCM (80 mL) and washed with brine (10 mL). The aqueous layer was further extracted with DCM (3 x 10 mL). The combined organic extracts were dried over anhydrous sodium sulfate, filtered, and concentrated in vacuo. The crude product was purified by flash column chromatography with pentane to give pentane (0.63 g) and TES 2 1 (2.52 g, 83%) in a mixture of O (0.81 g),...
Embodiment 2
[0275] Example 2.4-Azidobenzyl 2-diazo-3-oxo-4-((2R,3S)-4-oxo-3-((R)-1-((triethylsilyl )Oxy)ethyl)azetidin-2-yl)butyrate (12).
[0276] Overall synthesis scheme:
[0277]
[0278] step 1:
[0279]
[0280] Add LiAlH to the round bottom flask 4 (0.760 g, 19.9 mmol) and THF (40 mL). Methyl 4-aminobenzoate (2.00 g, 13.3 mmol) was dissolved in THF (5 mL), and the resulting solution was added dropwise to LiAlH at 0 °C 4 in solution. The reaction mixture was then warmed to room temperature and stirred for 3 hours. When TLC indicated the reaction was complete, the reaction was quenched with ethyl acetate (5 mL) and water (5 mL). HCl (3M aq.) was added until pH=7 was reached. The precipitate was filtered and washed with ethyl acetate. The combined liquids were concentrated, further diluted with ethyl acetate (90 mL), then washed with saturated NaHCO 3 (30 mL) solution and brine (30 mL) washed. The aqueous layer was further extracted with ethyl acetate (2 x 30 mL). The...
Embodiment 3
[0306] Example 3. (5R,6S)-6-((R)-1-hydroxyethyl)-3-((E)-3-(2-methoxy-4-(((3-oxo- 3H-phenoxazin-7-yl)oxy)methyl)phenoxy)prop-1-en-1-yl)-7-oxo-1-azabicyclo[3.2.0]hept-2- Preparation of ene-2-carboxylic acid (MCW-001).
[0307] Overall synthesis scheme:
[0308]
[0309] step 1:
[0310]
[0311] To a round bottom flask was added TES protected azetidinone 12 (105 mg, 0.216 mmol) and DCM (1.5 mL). Then add Rh 2 (C 7 h 15 CO 2 ) 4 (0.8 mg, 1 μmol), and the reaction mixture was stirred at reflux for 45 minutes. When TLC indicated the reaction was complete, the reaction mixture was concentrated and used directly in the next step. To the round bottom flask was added crude ketone and THF (1.2 mL) at -78 °C. Then DIPA (40 μL, 0.28 mmol) and NEt were added dropwise 3 (8.0 μL, 86 μmol), and the resulting solution was stirred for 10 minutes. Then add Tf dropwise 2 O (47 μL, 0.28 mmol), and the resulting mixture was stirred at -78° C. for 15 minutes. When TLC indicated tha...
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