ChemicalBook CAS DataBase List phenyl hydrogen ((((R)-1-(6-amino-9H-purin-9-yl)propan-2-yl)oxy)methyl)phosphonate

phenyl hydrogen ((((R)-1-(6-amino-9H-purin-9-yl)propan-2-yl)oxy)methyl)phosphonate synthesis

8synthesis methods

Product Name:phenyl hydrogen ((((R)-1-(6-amino-9H-purin-9-yl)propan-2-yl)oxy)methyl)phosphonate
CAS Number:379270-35-6
Molecular formula:C15H18N5O4P
Molecular Weight:363.31

147127-20-6
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108-95-2 Synthesis

108-95-2
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phenyl hydrogen ((((R)-1-(6-amino-9H-purin-9-yl)propan-2-yl)oxy)methyl)phosphonate

379270-35-6
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Yield:379270-35-6 93.63%

Reaction Conditions:

with pyridine;dicyclohexyl-carbodiimide at 70; for 4 h;

Steps:

1 Preparation method 2 of (R)-9-[2-(phosphoryl phenol methoxy) propyl] adenine
the compound represented by formula (I) (R)-9-[2-(phosphoryl methoxy) propyl] adenine (100.01g, 0.35mOl, 1.0eq, Zhejiang Supor Pharmaceutical Co., Ltd.) and phenol (65.50g, 0.70mol, 2.0eq, Xiqiao Chemical) dissolved into 1000ml of pyridine (Shanghai Titan Chemical Co., Ltd.), warm up at 70 ° C, added the drops of N,N’-dicyclohexylcarbodiimide (287.42g, 1.39mOl, 4.0eq, Suzhou Qifan Biotechnology Co., Ltd.) pyridine solution (500ml, Shanghai Titan Chemical Co., Ltd.), after the addition is completed, the reaction is carried out at 70 ° C for 4 hours, HPLC monitoring of the raw material reaction completely, cooling at room temperature, add 1500ml of ethyl acetate (Hangzhou Jiachen Chemical Co., Ltd.), filter, the filtrate is directly concentrated, added 1M sodium hydroxide (Zhejiang Sanying Chemical Reagent Co., Ltd.) solution to adjust the pH at 11~12, extracted three times with ethyl acetate (Hangzhou Jiachen Chemical Co., Ltd.) (100ml*3), and then by using 2M hydrochloric acid solution adjust the pH at 3 (Zhejiang Sanying Chemical Reagent Co., Ltd.), liquid was directly concentrated and then obtained the target product (118.42 g, yield 93.63%, containing a small amount of sodium chloride salt), HPLC purity was 68.54%.

References:

Hangzhou Heze Pharmaceutical Technology Co., Ltd.;Cai Liefeng;Jiang Weibin;Weng Deying CN104628773, 2018, B Location in patent:Paragraph 0021; 0062-0064

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101-02-0 Synthesis