ChemicalBook CAS DataBase List Sitagliptin N-Boc IMpurity

Sitagliptin N-Boc IMpurity synthesis

8synthesis methods

Product Name:Sitagliptin N-Boc IMpurity
CAS Number:486460-23-5
Molecular formula:C21H23F6N5O3
Molecular Weight:507.43

486460-00-8 Synthesis

Boc-(R)-3-Amino-4-(2,4,5-trifluorophenyl)butanoic acid

486460-00-8
347 suppliers
$14.00/5g

762240-92-6 Synthesis

3-(Trifluoromethyl)-5,6,7,8-tetrahydro-[1,2,4]triazolo[4,3-a]pyrazine hydrochloride

762240-92-6
545 suppliers
$25.00/1 g

486460-23-5
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Yield:486460-23-5 96%

Reaction Conditions:

with triethylamine;4-(4,6-dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium chloride in methanol at 20 - 50;Reagent/catalyst;Solvent;

Steps:

1 Example 1
(3R)-3-[(l,l-Dimemylethoxycarbonyl)ammo]-4-(2,4,5-trifluorophenyl)butanoic acid (10 g) is mixed with 4-(4,6-dimethoxy-l,3,5-triazin-2-yl)-4-methylmorpholinium chloride (10 g) in methanol (100 ml) at the laboratory temperature. 3-(Trifluoromethyl)-5,6,7,8-tetrahydro- [l,2,4]triazolo[4,3-a]pyrazine hydrochloride (7 g) is added to the resulting solution and triethylamine (4.7 ml) is added to the stirred suspension. During 2-3 minutes a solution is obtained that is further stirred at the laboratory temperature. After approximately 1 hour, white suspension of the product starts to separate. The reaction mixture is heated up to 50°C and distilled water (35 ml) is added to the resulting solution and the reaction mixture is cooled down to 15°C under stirring during 2 h. The separated product is filtered off and washed with 15 ml of a methanol/water (2/ 1 ) mixture. After drying the desired product is obtained with the yield of 96% and HPLC quality of >99%. Example 2

References:

ZENTIVA, K.S.;RICHTER, Jindrich;HALAMA, Ales;JIRMAN, Josef WO2014/86325, 2014, A1 Location in patent:Page/Page column 10

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