Tebipenem synthesis
- Product Name:Tebipenem
- CAS Number:161715-21-5
- Molecular formula:C16H21N3O4S2
- Molecular Weight:383.49
![4-Nitrobenzyl(1R,5S,6S)-6-[(R)-1-hydroxyethyl]-1-Methyl-2-[1-(1,3-thiazolin-2-yl)azetidin -3-yl]thio-1-carbapen-2-eM-3-carboxylate](/CAS/GIF/161715-20-4.gif)
161715-20-4
161715-21-5
The general procedure for the synthesis of (4R,5S,6S)-3-((1-(4,5-dihydrothiazol-2-yl)azetidin-3-yl)thio)-6-((R)-1-hydroxyethyl)-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid from tepipenem condensate is as follows: to compound (II) (R is p-nitrobenzyl ) (15.0 g, 29.0 mmol) was added 200 mL of n-butanol and 200 mL of water and stirred until completely dissolved. Subsequently 8.00 g of Raney Ni was added and the hydrogenation reaction was carried out at 60 °C. The reaction was carried out at 2.0 MPa hydrogen pressure and 20 °C for 4 hours. Upon completion of the reaction, the solid was collected by filtration and the filter cake was washed with 15 mL of water. The filtrate was adjusted to pH 6.5 with 4-dimethylaminopyridine and then washed with 150 mL of ethyl acetate. After the solution was cooled to 0 °C, 700 mL of acetone was added drop by drop and stirred for 10 minutes, 700 mL of acetone was again added drop by drop and stirring was continued for 1 hour. Finally, 12.5 g of white solid tebutamidine was obtained with a yield of 94.5% and a purity of 99.6%.
161715-20-4
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Yield: 94.5%
Reaction Conditions:
with hydrogen in water;butan-1-ol at 20; under 15001.5 Torr; for 4 h;Solvent;Pressure;Reagent/catalyst;
Steps:
1
The compound (II) (R is p-nitrobenzyl) (15.0 g, 29.Ommo 1) was added 200 mL of n-butanol, 200 mL of water, stirred to dissolve, and 8.00 g of Raney Ni was added and hydrogenated at 20 ° C under 2.0 MPa hydrogen pressure for 4 h. The filter cake was washed with 15 mL of water The filtrate was adjusted to pH 6.5 with 4-dimethylaminopyridine and then washed with 150 mL of ethyl acetate. After cooling to 0 ° C, 700 mL of acetone was added dropwise, stirred for 10 min and then 700 mL of acetone was added dropwise, stirred for 1 h, To give telbemidine as a white solid 12.5 g, yield 94.5%, purity 99.6%.
References:
Shanghai Institute of Pharmaceutical Industry;Luo, ying;Liu, xiangkui;Shen, yuhui;Zhu, xueyan;Yuan, zhedong CN102757430, 2016, B Location in patent:Paragraph 0040; 0041
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