Yaozh News Star Club Edu BBS TOP100 Customer Service APP
Iphone Download Android Download
  • English
  • 简体中文
Login Register
Search
Current Location： Home > Feedback Help Print

【结 构 式】

【分子编号】41094

【品名】methyl 4-[4-(1-azido-5,5,6,6,6-pentafluorohexyl)phenyl]butanoate

【CA登记号】

【 分 子 式 】C17H20F5N3O2

【 分 子 量 】393.356836

【元素组成】C 51.91% H 5.12% F 24.15% N 10.68% O 8.13%
与该中间体有关的原料药合成路线共 2 条
合成路线1合成路线2

合成路线1

该中间体在本合成路线中的序号：(IX)

Friedel-Crafts acylation of methyl 4-phenylbutyrate (I) with 5,5,6,6,6-pentafluorohexanoyl chloride (II) in the presence of AlCl3 produced ketone (III). This was converted to oxime (IV) upon treatment with hydroxylamine hydrochloride and pyridine, and subsequently reduced to amine (V) by catalytic hydrogenation over Raney nickel. Alternatively, ketone (III) was reduced to alcohol (VI) employing NaBH4. Chlorination of (VI) with SOCl2, followed by displacement with NaN3 furnished azide (VII). Then, reduction of the azido group of (VII) by means of PPh3 provided an alternative route to amine (V). Acylation of amine (V) with 4-fluorobenzenesulfonyl chloride (VIII) gave rise to sulfonamide (IX). The methyl ester group of (IX) was finally hydrolyzed with NaOH yielding the title carboxylic acid.

参考文献 中间体
合成目标
【1】 Yasuda, S.; Ogawa, N.; Sakurai, S. (Hokuriku Seiyaku Co., Ltd.); Benzenesulfonamide derivs. and drugs containing the same. EP 0943606; JP 1998195038; WO 9821177 .
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) 41088 methyl 4-phenylbutanoate 2046-17-5 C11H14O2 详情 详情
(II) 41089 5,5,6,6,6-pentafluorohexanoyl chloride C6H6ClF5O 详情 详情
(III) 41090 methyl 4-[4-(5,5,6,6,6-pentafluorohexanoyl)phenyl]butanoate C17H19F5O3 详情 详情
(IV) 41091 methyl 4-[4-(5,5,6,6,6-pentafluorohexanimidoyl)phenyl]butanoate C17H20F5NO3 详情 详情
(V) 41092 methyl 4-[4-(1-amino-5,5,6,6,6-pentafluorohexyl)phenyl]butanoate C17H22F5NO2 详情 详情
(VI) 41093 methyl 4-[4-(5,5,6,6,6-pentafluoro-1-hydroxyhexyl)phenyl]butanoate C17H21F5O3 详情 详情
(VII) 41094 methyl 4-[4-(1-azido-5,5,6,6,6-pentafluorohexyl)phenyl]butanoate C17H20F5N3O2 详情 详情
(VIII) 12292 4-Fluorobenzenesulfonyl chloride 349-88-2 C6H4ClFO2S 详情 详情
(IX) 41094 methyl 4-[4-(1-azido-5,5,6,6,6-pentafluorohexyl)phenyl]butanoate C17H20F5N3O2 详情 详情

合成路线2

该中间体在本合成路线中的序号：(VII)

Friedel-Crafts acylation of methyl 4-phenylbutyrate (I) with 5,5,6,6,6-pentafluorohexanoyl chloride (II) in the presence of AlCl3 produced ketone (III). This was converted to oxime (IV) upon treatment with hydroxylamine hydrochloride and pyridine, and subsequently reduced to amine (V) by catalytic hydrogenation over Raney nickel. Alternatively, ketone (III) was reduced to alcohol (VI) employing NaBH4. Chlorination of (VI) with SOCl2, followed by displacement with NaN3 furnished azide (VII). Then, reduction of the azido group of (VII) by means of PPh3 provided an alternative route to amine (V). Acylation of amine (V) with 4-fluorobenzenesulfonyl chloride (VIII) gave rise to sulfonamide (IX). The methyl ester group of (IX) was finally hydrolyzed with NaOH yielding the title carboxylic acid.

参考文献 中间体
合成目标
【1】 Yasuda, S.; Ogawa, N.; Sakurai, S. (Hokuriku Seiyaku Co., Ltd.); Benzenesulfonamide derivs. and drugs containing the same. EP 0943606; JP 1998195038; WO 9821177 .
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) 41088 methyl 4-phenylbutanoate 2046-17-5 C11H14O2 详情 详情
(II) 41089 5,5,6,6,6-pentafluorohexanoyl chloride C6H6ClF5O 详情 详情
(III) 41090 methyl 4-[4-(5,5,6,6,6-pentafluorohexanoyl)phenyl]butanoate C17H19F5O3 详情 详情
(IV) 41091 methyl 4-[4-(5,5,6,6,6-pentafluorohexanimidoyl)phenyl]butanoate C17H20F5NO3 详情 详情
(V) 41092 methyl 4-[4-(1-amino-5,5,6,6,6-pentafluorohexyl)phenyl]butanoate C17H22F5NO2 详情 详情
(VI) 41093 methyl 4-[4-(5,5,6,6,6-pentafluoro-1-hydroxyhexyl)phenyl]butanoate C17H21F5O3 详情 详情
(VII) 41094 methyl 4-[4-(1-azido-5,5,6,6,6-pentafluorohexyl)phenyl]butanoate C17H20F5N3O2 详情 详情
(VIII) 12292 4-Fluorobenzenesulfonyl chloride 349-88-2 C6H4ClFO2S 详情 详情
(IX) 41094 methyl 4-[4-(1-azido-5,5,6,6,6-pentafluorohexyl)phenyl]butanoate C17H20F5N3O2 详情 详情
Extended Information