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【结 构 式】 
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【分子编号】21411 【品名】2-chloro-1-ethanamine hydrochloride 【CA登记号】870-24-6 |
【 分 子 式 】C2H7Cl2N 【 分 子 量 】115.98972 【元素组成】C 20.71% H 6.08% Cl 61.13% N 12.08% |
合成路线1
该中间体在本合成路线中的序号：(III)Title compound was prepared by formation of the arachidonic acid chloride (II) upon treatment of the corresponding acid (I) with oxalyl chloride in CH2Cl2 containing DMF at 0 C, followed by condensation with 2-chloroethylamine - HCl (III) in the presence of pyridine.
| 【1】 Lin, S.; Khanolkar, A.D.; Fan, P.; Goutopoulos, A.; Qin, C.; Papahadjis, D.; Makriyannis, A.; Novel analogues of arachidonylethanolamide (anandamide): Affinities for the CB1 and CB2 cannabinoid receptors and metabolic stability. J Med Chem 1998, 41, 27, 5353. |
合成路线2
该中间体在本合成路线中的序号：(II)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 |