(1R, 2S)-fluorocyclopropylamine hydrochloride Used For Sitafloxacin CAS 141042-21-9

Name: (1R, 2S)-fluorocyclopropylamine hydrochloride Used For Sitafloxacin CAS 141042-21-9
Brand: Taizhou Volsen Chemical Co., Ltd.
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Model No. :	141042-21-9
Brand Name :	VOLSENCHEM

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Taizhou, Zhejiang, China

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Product description

Sitafloxacin side chain intermediate (1R, 2S)-fluorocyclopropylamine hydrochloride CAS number is 141042-21-9, his synthesis process is as below:
1. Synthesis of a three-membered ring. 1 kg of methyl 4-chloroacetoacetate was dissolved in 6 L of acetonitrile, and 38 g of valine and 1.25 kg of 1,2-dibromoethane were added, and a total of 2.3 kg of potassium carbonate was added in 10 portions with stirring, and then the reaction solution was stirred at 35 ° C. hour. Filtration and concentration of the filtrate under reduced pressure afforded a hexanes.
2. Synthesis of nitrogen heterocycles. The colorless oily three-membered carbocyclic compound obtained in the step 1 was continuously added to 5 L of a 25% aqueous ammonia solution, stirred for 3 hours, and then heated to 40 ° C, and the reaction was continued for 10 hours. It was suction filtered, washed with solid water, and dried to obtain 300 g of a white solid powdery five-membered nitrogen heterocyclic compound.
3. Generate chiral carbon. The white solid powdery five-membered nitrogen heterocyclic compound obtained in the step 2 was dissolved in 2 L of toluene, and then 333 g of R-1-phenylethylamine was added thereto, and the mixture was refluxed for 10 hours under stirring. It was cooled, concentrated to dryness under reduced pressure to give a solid compound.
4. Restore. The solid chiral compound obtained in the step 3 was dissolved in 2 L of methanol, stirred, and after completely dissolved, the system was placed in an ice bath, and stirring was continued, and 209 g of sodium borohydride was slowly added. The ice bath temperature was maintained for 1 hour, then slowly warmed to 30℃, and reacted at this temperature for 5 hours. 1 L of a saturated aqueous solution of sodium hydrogencarbonate was added, and the mixture was evaporated to dryness. 430 g of a white solid chiral compound were obtained.
5. Upper protecting group. To the 408 g of the white solid chiral compound obtained in the step 4, 20 g of di-tert-butyl dicarbonate and 3 L of methanol were added, and the mixture was stirred until completely dissolved. 21 g of 5% Pd/C was added, and the air in the system was repeatedly substituted 4 times with hydrogen. It was pressurized to 10 atm and reacted under a hydrogen atmosphere for 24 hours. The mixture was suction filtered, concentrated to dryness, and the residue was crystallised from ethyl acetate and petroleum ether to give 338 g of a white solid solid.
6. Carbonyl reduction. The white solid-state protective group-containing chiral compound obtained in the step 5 was dissolved in 2.5 L of anhydrous tetrahydrofuran, and the reaction system was placed in an ice bath under a nitrogen atmosphere, and 10 mol/L of borane dimethyl sulfide was added dropwise. After the completion of the dropwise addition, the mixture was slowly warmed to room temperature, and reacted for 15 hours. Then, 500 ml of methanol was slowly added dropwise thereto, and the mixture was stirred for 2 hours, and then slowly heated to 50 ° C and stirred for 5 hours. The organic layer was extracted with EtOAc (3 mL). 2L of petroleum ether was added to the residue and stirred and beaten. Filtration, the solid was washed with cold petroleum ether, and the solid was collected and dried to give 253 g of the title compound, which is the Sitafloxacin side chain intermediate (1R, 2S)-fluorocyclopropylamine hydrochloride CAS 141042-21-9.

Thera. Category: antibiotic

Cas No.:127254-10-8

Synonyms:Cis-2-fluorocyclopropylaminetosylate

141042-21-9