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HomeProductsPharmaceutical IntermediatesAnti-DiabetesSynthesis Process Of Omarigliptin Intermediate CAS 951127-25-6

Synthesis Process Of Omarigliptin Intermediate CAS 951127-25-6

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Model No. 951127-25-6


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Place of OriginCHINA



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Omarigliptin intermediate CAS number 951127-25-6, also as know as CPo3604-01 intermediate,molecular formula: C16H19F2NO4, molecular weight: 327.32, his synthesis process is as following:
31.2g NaOH was dissolved in water and methanol mixture, the ethanol refrigerant was cooled to 0℃, and after 30 minutes, 57.3 ml of 2,5-difluorobenzaldehyde and 42.6 ml of nitromethane were added dropwise. After the reaction, The mixture was neutralized with acetic acid, stirred with ethyl acetate, and the organic layer was washed successively with sodium carbonate solution and brine, dried over anhydrous sodium sulfate, filtered and concentrated to give 2-nitro-1 (2,5- 112 g of difluorophenyl)-ethanol, hereinafter referred to as intermediate I.
100g of intermediate I was dissolved in 200ml of acetone and cooled to 0℃, 90g of Jones reagent was added dropwise, the temperature of the reaction solution was maintained at 3 ℃, after the reaction was completed, the reaction solution was cooled to below 0 ℃ and 50 ml of isopropanol was added dropwise to destroy the excess. Jones reagent, filtered and washed with acetone, the filtrate and washing liquid were combined, evaporated to dryness to give a clear green oily liquid, which was cooled in an ice bath, and 1 L of cold water was added to precipitate a white solid, which was filtered and washed with water and dried to give 2-nitro-1 (2) , 5-difluorophenyl)-acetaldehyde 62.3 g, hereinafter referred to as intermediate II.
50.85 ml of 1,3-dichloro-2-propanol and 54.7 g of the intermediate II were dissolved in DMF, and 176 g of Cs2CO3 was added thereto, and reacted at 25 to 30 ℃ for 4 hours, and the reaction liquid was filtered, and the residue was washed with diisopropyl ether. The filtrate was poured into 1.75 L/1 N of cold hydrochloric acid, and extracted twice with 850 ml of isopropyl ether. The extract was washed with saturated brine, and the layers were separated. The solvent was evaporated to dryness. The mixture was washed and dried to give 37.1 g of 2-(2,5-difluorophenyl)-3-nitro-5-hydroxytetrahydro-pyran, hereinafter referred to as intermediate III.
35.6g of intermediate III was dissolved in 125ml of methanol, 16g of NaBH4 was added in batches within 30min, the temperature was controlled at 0-5°C, and the mixture was stirred at 0-5°C for 30min after the addition, then 0.5L/6N HCl was added dropwise to terminate the reaction. 1.05L of ice water, stirred at 0 ℃ and precipitated as a white solid, filtered, washed with water and dried to give 2-(2,5-difluorophenyl)-3-nitro-5-hydroxytetrahydro-pyranose.The solid obtained above was added to 92 ml of isopropanol, heated to 92 ℃ to dissolve, and then slowly cooled to precipitate trans-2-(2,5-difluorophenyl)-3-nitro-5-hydroxytetrahydro- Pyran, filtered, washed with isopropanol, dried to give a trans product of 16.9 g. The filtrate was concentrated to dryness. The residue was combined with THF . The solvent was evaporated to give the diastereomer (13.4 g). Treatment with isopropanol by the method described above gave 7.4 g of trans-2-(2,5-difluorophenyl)-3-nitro-5-hydroxytetrahydro-pyran. Adding 100 ml of isopropanol to 24.3 g of trans-2-(2,5-difluorophenyl)-3-nitro-5-hydroxytetrahydro-pyran obtained in the above two steps, heating to 90 ℃ to dissolve, and then It was cooled to room temperature, crystallized, filtered, washed with isopropyl alcohol and dried to give 21.5 g of trans-2-(2,5-difluorophenyl)-3-nitro-5-hydroxytetrahydro-pyran, below Referred to as intermediate IV.
20.7 g of intermediate IV was dissolved in 100 ml of methanol, added to a high pressure reaction vessel, 3 g of Raney Ni catalyst was added, hydrogen was replaced, H 2 pressure was 2.5 MPa, 40 ℃, and the reaction was filtered for 3 h, and the filtrate was desolvated to obtain trans-2. - (2,5-Difluorophenyl)-3-amino-5-hydroxytetrahydro-2H-pyran crude 18.7 g, hereinafter referred to as intermediate V.
10.5 g of D(-) tartaric acid was dissolved in 100 ml of methanol, and a mixture of 17 g of intermediate V and 59.5 ml of methanol was added thereto, stirred at 25 ℃ for 15 h, filtered, washed with methanol and dried, and the obtained solid was refluxed in 119 ml of methanol. 1 h, slowly cool to room temperature and stir for 15 h. The solid was filtered again, washed with methanol and dried to give 14.2 g of tart. The obtained tartaric acid salt was dissolved in 200 ml of a mixed solvent of acetonitrile and water, 10 g of Na2CO3 was added in portions at 25-30 ℃, the reaction solution was cooled to 0-5 ℃, and 15.3 g of BOC was further added. After stirring for 2 hours, acetonitrile was distilled off, and the residual solution was distilled. 150 ml of ice water was added and stirred for 30 min, and the solid was filtered and washed with water and dried to give a white solid (2R,3S)-2-(2,5-difluorophenyl)-5-hydroxytetrahydro-2H-pyran- 11.7 g of tert-butyl 3-carbamic acid, hereinafter referred to as intermediate VI.
10 g of the intermediate VI was dissolved in 50 ml of dichloromethane, and 6 g of CrO3 was added thereto, and the mixture was stirred at room temperature for 3 hours, allowed to stand, and the layers were separated. The organic phases were combined and washed with 10% Na2S2O3, water, and brine. The organic phase was dried over anhydrous sodium sulfate and evaporated to dryness to give Omarigliptin intermediate.
The quality Specification of the N-[(2R,3S)-2-(2,5-difluorophenyl)tetrahydro-5-oxo-2H-pyran-3-yl]-CarbaMic acid 1,1-diMethylethyl ester CAS 951127-25-6 is total impurity ≤1.0%, single impurity ≤0.50%, loss on drying ≤0.50%.

Thera. Category:Anti Diabetes

Cas No.: 951127-25-6

Synonym: CPo3604-01;tert-butyl [(2R,3S)-5-oxo-2-(2,5-difluorophenyl)tetradihydro-2H-pyran-3-yl]carbaMate;tert-butyl [(2R,3S)-2-(2,5-difluorophenyl)-5-oxotetrahydro-2H-pvran-3 yl]carbaMate;tert-butyl ((2R,3S)-2-(2,5-difluorophenyl)-5-oxotetrahydro-2H-pyran-3-yl)carbaMate;N-[(2R,3S)-2-(2,5-difluorophenyl)tetrahydro-5-oxo-2H-pyran-3-yl]-CarbaMic acid 1,1-diMethylethyl ester;Product NaMe:MK-3102 interMediate;Omarigliptin inter.

Molecular Formula:C16H19F2NO4


Molecular Weight:327.32

Assay: ≥98.%

Appearance: White Crystalline solid

Storage: normal

Packing:Export worthy packing

Material Safety Data Sheet:Available on request

Related Intermediate:

1)N-[(2R,3S)-2-(2,5-difluorophenyl)tetrahydro-5-oxo-2H-pyran-3-yl]-CarbaMic acid 1,1-diMethylethyl ester 951127-25-6

2)2-(Methylsulfonyl)-2,4,5,6-tetrahydropyrrolo[3,4-c]pyrazole, CAS 1280210-80-1,

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