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【结 构 式】

【分子编号】66026

【品名】Dichlorophosphoryloxymethylbenzene; Phosphorodichloridic acid, phenylmethyl ester

【CA登记号】52692-02-1

【 分 子 式 】C7H7Cl2O2P

【 分 子 量 】225.010542

【元素组成】C 37.37% H 3.14% Cl 31.51% O 14.22% P 13.77%

与该中间体有关的原料药合成路线共 1 条

合成路线1

该中间体在本合成路线中的序号:(V)

The condensation of phenyl dichlorophosphonate (I) with 2-chloroethylamine hydrochloride (II) in the presence of Et3N in cold CH2Cl2 provides phenyl N,N ’-bis(2-chloroethyl)phosphorodiamidate (III), which is finally converted to the corresponding phosphorodiamidic acid by catalytic hydrogenation over PtO2 in EtOH . In an alternative method, acylation of benzyl alcohol (IV) with POCl3 in the presence of Et3N in cold acetonitrile gives benzyl dichlorophosphonate (V), which is further condensed with 2-chloroethylamine hydrochloride (II) in the presence of Et3N to yield benzyl N,N’-bis(2-chloroethyl)phosphorodiamidate (VI). Finally, benzyl ester (VI) is then submitted to hydrogenolysis over Pd/C in acetonitrile .

1 Morgan, L. (Dekk-Tec, Inc.). Salts of isophosphoramide mustard and analogs thereof as anti-tumor agents. EP 1805192, JP 2008517929, US 2006089333, US 2008267945, WO 2006047575.
2 Amedio, J.C., Wallner, B.P., Komarnitsky, P.B. (ZIOPHARM Oncology, Inc.). Salts of isophosphoramide mustard and analogs thereof. EP 2155682, JP 2010523571, US 2008255056, WO 2008124097.
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
(I) 39640 Phenyl dichlorophosphate;phenyl phosphorodichloridate 770-12-7 C6H5Cl2O2P 详情 详情
(II) 21411 2-chloro-1-ethanamine hydrochloride 870-24-6 C2H7Cl2N 详情 详情
(III) 39641 Phenyl N,N'-Bis(2-Chloroethyl)Phosphorodiamidate; 2-Chloroethyl-[(2-Chloroethylamino)-(Phenoxy)Phosphoryl]Amine; Nsc318225 70772-68-8 C10H15Cl2N2O2P 详情 详情
(IV) 18710 Benzyl alcohol; Phenylmethanol 100-51-6 C7H8O 详情 详情
(V) 66026 Dichlorophosphoryloxymethylbenzene; Phosphorodichloridic acid, phenylmethyl ester 52692-02-1 C7H7Cl2O2P 详情 详情
(VI) 66027 Benzyl N,N'-Bis(2-Chloroethyl)Phosphorodiamidate; 2-Chloroethyl-[(2-Chloroethylamino)-(Benzyloxy)Phosphoryl]Amine   C11H17Cl2N2O2P 详情 详情
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