(-)-(S)-Bromofosfamide, CBM-11
Chemical Name: 3-(2-Bromoethyl)-N-(2-chloroethyl)-2H-tetrahydro-1,3,2-oxazaphosphorin-2-amine 2-oxide
CAS No. 146452-37-1
项目整合开发状态: Phase II
项目研究机构: Polish Academy of Science (Originator)
合成路线:Condensation of the chiral 2-chloro-3-(alpha-methylbenzyl)tetrahydro-2H-1,3,2-oxaazaphosphorine 2-oxide (I) with 2-chloroethylamine (II) afforded the 2-(chloroethylamino) derivative (III).The chiral auxiliary group of (III) was then removed by catalytic hydrogenation with H2 over -Pd/C yielding (R)-2-(2-chloroethylamino)tetrahydro-2H-1,3,2-oxaazaphosphorine 2-oxide (IV).Acylation of (IV) with bromoacetyl bromide (V) in the presence of triethylamine hydrobromide furnished bromoacetamide (VI).The amide carbonyl group of (VI) was finally reduced by treatment with NaBH4 and BF3稥t2O.
📌 参考资料/链接：
参考文献标题:Process for the production of the derivs.of 1,3,2-oxazaphosphorinane
文献作者:Kutner,A.; Grynkiewicz,G.; Stec,W.J.; Radzikowski,C.; Szelejeswki,W.; Kinas,R.; Misiura,K.; Grodner,J.; Kusnierczyk,H.; Pilichowska,S.
参考来源:EP 0295576
📄 详细内容
合成路线:Condensation of the chiral 2-chloro-3-(alpha-methylbenzyl)tetrahydro-2H-1,3,2-oxaazaphosphorine 2-oxide (I) with 2-chloroethylamine (II) afforded the 2-(chloroethylamino) derivative (III).The chiral auxiliary group of (III) was then removed by catalytic hydrogenation with H2 over -Pd/C yielding (R)-2-(2-chloroethylamino)tetrahydro-2H-1,3,2-oxaazaphosphorine 2-oxide (IV).Acylation of (IV) with bromoacetyl bromide (V) in the presence of triethylamine hydrobromide furnished bromoacetamide (VI).The amide carbonyl group of (VI) was finally reduced by treatment with NaBH4 and BF3稥t2O.
参考文献标题:(S)-(-)-Bromofosfamide (CBM-11): Synthesis and antitumor activity and cytotoxicity in mice
文献作者:Misiura,K.; Kinas,R.W.; Kusnierczyk,H.; Radzikowski,C.; Stec,W.J.
参考来源:Anti-Cancer Drugs 2001,12(5),453
产品链接: CAS No. 146452-37-1››