Broad-spectrum carbapenems
A kind of alkenyl compound technology, applied in organic chemistry, pharmaceutical formulation, antibacterial drugs, etc., can solve problems such as inactivity and clinical failure
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[0543] Compound preparation
[0544]Described herein are compounds, or pharmaceutically acceptable salts, solvates, or stereoisomers thereof, which are useful in the treatment of bacterial infections, and methods for their preparation. In some embodiments, a compound described herein, or a pharmaceutically acceptable salt, solvate, or stereoisomer thereof, is synthesized using standard synthetic reactions known to those of skill in the art or using methods known in the art. These reactions can be used in a linear sequence to provide compounds, or they can be used to synthesize fragments that are subsequently ligated by methods known in the art. In some embodiments, starting materials used in the synthesis of compounds described herein are synthesized or obtained from sources such as, but not limited to, Aldrich Chemical Co. (Milwaukee, Wisconsin), Bachem (Torrance, California), or Sigma Chemical Co. (St. Louis, Mo.) from commercial sources. In some embodiments, the compounds...
Embodiment 1
[0582] Example 1: (4R,5S,6S)-6-((R)-1-hydroxyethyl)-4-methyl-7-oxo-3-(((R)-1-(piperidine- 4-yl)pyrrolidin-3-yl)thio)-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid.
[0583]
[0584] Step 1: Synthesis of (S)-tert-butyl 3-((methylsulfonyl)oxy)pyrrolidine-1-carboxylate.
[0585]
[0586] To a solution of (S)-Boc-3-pyrrolidinol (8.42 g, 45 mmol) in DCM (150 mL) at 0 °C was added triethylamine (9.5 mL, 68.2 mmol) followed by methanesulfonyl chloride (4 mL, 50.8 mmol). The reaction mixture was stirred at 0 °C for 30 min, then warmed to room temperature for 30 min, and washed with saturated NaHCO 3 Washed with aqueous solution, Na 2 SO 4 Drying and concentration in vacuo gave the crude product which was used in the next step without further purification.
[0587] Step 2: Synthesis of (R)-tert-butyl 3-(acetylthio)pyrrolidine-1-carboxylate.
[0588]
[0589] To a solution of the crude formate in acetone (380 mL) was added potassium thioacetate (7.8 g, 68.3 mmol). The ...
Embodiment 2
[0608] Example 2: (4R,5S,6S)-6-((R)-1-hydroxyethyl)-4-methyl-7-oxo-3-(((S)-1-(piperidine- 4-yl)pyrrolidin-3-yl)thio)-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid.
[0609]
[0610] Except using (R)-Boc-3-pyrrolidinol instead of (S)-Boc-3-pyrrolidinol as the starting material in step 1, the target compound was prepared according to the same reaction procedure as described in Example 1 . ESI-MS m / z 396(MH) + .
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