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【结 构 式】 
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【分子编号】56224 【品名】2-[(2-chloroethyl)amino]-1,3,2lambda~5~-oxazaphosphinan-2-one 【CA登记号】 |
【 分 子 式 】C5H12ClN2O2P 【 分 子 量 】198.589022 【元素组成】C 30.24% H 6.09% Cl 17.85% N 14.11% O 16.11% P 15.6% |
合成路线1
该中间体在本合成路线中的序号：(IV)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·Et2O.
| 【1】 Kinas, R.W.; Stec, W.J.; Kusnierczyk, H.; Misiura, K.; radzikowski, C.; (S)-(-)-Bromofosfamide (CBM-11): Synthesis and antitumor activity and cytotoxicity in mice. Anti-Cancer Drugs 2001, 12, 5, 453. |
| 【2】 Kutner, A.; Grynkiewicz, G.; Stec, W.J.; Radzikowski, C.; Szelejeswki, W.; Kinas, R.; Misiura, K.; Grodner, J.; Kusnierczyk, H.; Pilichowska, S.; Process for the production of the derivs. of 1,3,2-oxazaphosphorinane. EP 0295576 . |
| 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) | 56222 | 2-chloro-3-[(1S)-1-phenylethyl]-1,3,2lambda~5~-oxazaphosphinan-2-one | C11H15ClNO2P | 详情 | 详情 | |
| (II) | 33455 | 2-chloro-1-ethanamine; 2-chloroethylamine | C2H6ClN | 详情 | 详情 | |
| (III) | 56223 | 2-[(2-chloroethyl)amino]-3-[(1S)-1-phenylethyl]-1,3,2lambda~5~-oxazaphosphinan-2-one | C13H20ClN2O2P | 详情 | 详情 | |
| (IV) | 56224 | 2-[(2-chloroethyl)amino]-1,3,2lambda~5~-oxazaphosphinan-2-one | C5H12ClN2O2P | 详情 | 详情 | |
| (V) | 14005 | 2-Bromoacetyl bromide; Bromoacetyl bromide | 598-21-0 | C2H2Br2O | 详情 | 详情 |
| (VI) | 56225 | 3-(2-bromoacetyl)-2-[(2-chloroethyl)amino]-1,3,2lambda~5~-oxazaphosphinan-2-one | C7H13BrClN2O3P | 详情 | 详情 |