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【结 构 式】 
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【分子编号】10433 【品名】methyl 2-[[2-(5-chloro-2-phenoxyphenyl)acetyl](methyl)amino]acetate 【CA登记号】 |
【 分 子 式 】C18H18ClNO4 【 分 子 量 】347.79796 【元素组成】C 62.16% H 5.22% Cl 10.19% N 4.03% O 18.4% |
合成路线1
该中间体在本合成路线中的序号：(XIX)7) [12b-14C]-Org-5222: The condensation of labeled sarcosine methyl ester (XVI) (prepared from sarcosine (XV) with SOCl2 and methanol) with 2-(5-chloro-2-phenoxyphenyl)acetyl chloride (XVIII) (prepared from the corresponding acid (XVII) and SOCl2) yields the acylated sarcosine (XIX), which is cyclized by means of potassium tert-butoxide in toluene to the pyrrolidinedione (XX). A further cyclization of (XX) with polyphosphoric acid affords [3a-14C]-11-chloro-2-methyl-2,3-dihydro-1H-dibenz[2,3:6,7]oxepino[4,5-c]pyrrol-1-one (XXI), which is reduced with Mg in methanol to the trans-isomeric amide (XXII) (along with the cis-isomer, which is separated by HPLC). Finally, the amide (XXII) is reduced with LiAlH4/AlCl3 in ethyl ether.
| 【1】 Wagenaars, G.; Vader, J.; Sperling, E.; Terpstra, A.; Kaspersen, F.; Hilberink, P.; Schlachter, I.; The syntheses of radiolabelled Org 5222 and its main metabolite Org 30526. J Label Compd Radiopharm 1994, 34, 9, 845. |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| (XXIIa) | 10436 | (3aS,12bS)-11-Chloro-2-methyl-2,3,3a,12b-tetrahydro-1H-dibenzo[2,3:6,7]oxepino[4,5-c]pyrrol-1-one | C17H14ClNO2 | 详情 | 详情 | |
| (XXIIb) | 44653 | (3aS,12bR)-11-chloro-2-methyl-2,3,3a,12b-tetrahydro-1H-dibenzo[2,3:6,7]oxepino[4,5-c]pyrrol-1-one | C17H14ClNO2 | 详情 | 详情 | |
| (XXIIa) | 44659 | (3aS,12bS)-11-chloro-2-methyl-2,3,3a,12b-tetrahydro-1H-dibenzo[2,3:6,7]oxepino[4,5-c]pyrrol-1-one | C17H14ClNO2 | 详情 | 详情 | |
| (XXIIb) | 44660 | (3aS,12bR)-11-chloro-2-methyl-2,3,3a,12b-tetrahydro-1H-dibenzo[2,3:6,7]oxepino[4,5-c]pyrrol-1-one | C17H14ClNO2 | 详情 | 详情 | |
| (XV) | 10429 | N-Methylglycine; Sarcosine; 2-(Methylamino)acetic acid | 107-97-1 | C3H7NO2 | 详情 | 详情 |
| (XV) | 44654 | 2-(methylamino)acetic acid | C3H7NO2 | 详情 | 详情 | |
| (XVI) | 10430 | methyl 2-(methylamino)acetate; methyl N-methylglycinate | 5473-12-1 | C4H9NO2 | 详情 | 详情 |
| (XVI) | 44655 | methyl 2-(methylamino)acetate | C4H9NO2 | 详情 | 详情 | |
| (XVII) | 10431 | 2-(5-Chloro-2-phenoxyphenyl)acetic acid | C14H11ClO3 | 详情 | 详情 | |
| (XVIII) | 10432 | 2-(5-Chloro-2-phenoxyphenyl)acetyl chloride | C14H10Cl2O2 | 详情 | 详情 | |
| (XIX) | 10433 | methyl 2-[[2-(5-chloro-2-phenoxyphenyl)acetyl](methyl)amino]acetate | C18H18ClNO4 | 详情 | 详情 | |
| (XIX) | 44656 | methyl 2-[[2-(5-chloro-2-phenoxyphenyl)acetyl](methyl)amino]acetate | C18H18ClNO4 | 详情 | 详情 | |
| (XX) | 10434 | 3-(5-Chloro-2-phenoxyphenyl)-1-methyl-2,4-pyrrolidinedione | C17H14ClNO3 | 详情 | 详情 | |
| (XX) | 44657 | 3-(5-chloro-2-phenoxyphenyl)-1-methyl-2,4-pyrrolidinedione | C17H14ClNO3 | 详情 | 详情 | |
| (XXI) | 10435 | 11-Chloro-2-methyl-2,3-dihydro-1H-dibenzo[2,3:6,7]oxepino[4,5-c]pyrrol-1-one | C17H12ClNO2 | 详情 | 详情 | |
| (XXI) | 44658 | 11-chloro-2-methyl-2,3-dihydro-1H-dibenzo[2,3:6,7]oxepino[4,5-c]pyrrol-1-one | C17H12ClNO2 | 详情 | 详情 |