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【结 构 式】

【分子编号】10432

【品名】2-(5-Chloro-2-phenoxyphenyl)acetyl chloride

【CA登记号】

【 分 子 式 】C14H10Cl2O2

【 分 子 量 】281.1376

【元素组成】C 59.81% H 3.59% Cl 25.22% O 11.38%

与该中间体有关的原料药合成路线共 2 条

合成路线1

该中间体在本合成路线中的序号:(XVIII)

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

合成路线2

该中间体在本合成路线中的序号:(II)

 

1 Van der Linden M, Roeters T, Harting R, et al. 2008. Debottlenecking the synthesis route of asenapine. Organic Process Reasearch & Development, 12: 196.
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) 10431 2-(5-Chloro-2-phenoxyphenyl)acetic acid C14H11ClO3 详情 详情
(II) 10432 2-(5-Chloro-2-phenoxyphenyl)acetyl chloride C14H10Cl2O2 详情 详情
(III) 10430 methyl 2-(methylamino)acetate; methyl N-methylglycinate 5473-12-1 C4H9NO2 详情 详情
(IV) 44656 methyl 2-[[2-(5-chloro-2-phenoxyphenyl)acetyl](methyl)amino]acetate C18H18ClNO4 详情 详情
(V) 10434 3-(5-Chloro-2-phenoxyphenyl)-1-methyl-2,4-pyrrolidinedione C17H14ClNO3 详情 详情
(VI) 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
(VII) 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
(VIII) 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
Extended Information