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ChemicalBook CAS DataBase List Edoxaban Impurity 16
480450-69-9

Edoxaban Impurity 16 synthesis

11synthesis methods
-

Yield: 75.9%

Reaction Conditions:

Stage #1:(1S,3R,4R)-3-[(tert-butoxycarbonyl)amino]-4-hydroxy-N,N-dimethylcyclohexanecarboxamide with diphenyl phosphoryl azide;1,8-diazabicyclo[5.4.0]undec-7-ene in toluene at 45 - 50;
Stage #2: with potassium carbonate in toluene at 100 - 105;

Steps:

2 Example 2 Synthesis of tert-butyl N-[(1R,2S,5S)-2-azido-5-[(dimethylamino)carbonyl]cyclohexyl]carbamate
Toluene (3000g) was added to the reaction flask, then 109B6-01 (600g; 2.095mol) was added, DBU (420g; 2.759mol) was added, and diphenyl azide phosphate (DPPA) (750g; 2.725mol) was added. Heat to 45-50°C to react for 2-3hrs, then add anhydrous potassium carbonate (500g; 3.618mol), continue to heat up to 100-105°C, stir and react for 36-40hr.After the reaction is completed, cool to 4050, add water (3000g) to the reaction system, keep it at 4045, stir and extract, keep the water phase at 4045, and extract three times with toluene (1200g+600g× 2); Combine the organic phases; dry with anhydrous sodium sulfate, filter, collect the filtrate, and concentrate toluene under reduced pressure to obtain a residue; add ethyl acetate and n-heptane (1:3, w/w) to the residue , Stir and crystallize at room temperature; filter, collect the solid, and dry to obtain 109B8-01 with a dry weight of about 495g. Yield: 75.9% (theoretical amount: 652.40 g).

References:

Inner Mongolia Jingdong Pharmaceutical Co., Ltd.;Lv Guanfeng;Xiao Jiang;Guo Rongyao CN111606827, 2020, A Location in patent:Paragraph 0046-0048

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