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【结 构 式】

【分子编号】44599

【品名】methyl 4-(2-oxopropyl)benzoate

【CA登记号】

【 分 子 式 】C11H12O3

【 分 子 量 】192.21448

【元素组成】C 68.74% H 6.29% O 24.97%

与该中间体有关的原料药合成路线共 1 条

合成路线1

该中间体在本合成路线中的序号:(VIII)

The synthesis of [14C]-labeled BRL-26830A has been described: The reaction of copper sulfate (I) with sodium methabisulfite, followed by treatment with [14C]-labeled potassium cyanide (II) yields cuprous cyanide (III), which is condensed with methyl 4-bromobenzoate (IV) to afford methyl 4-cyanobenzoate (V). The reduction of (V) with Al/Ni and formic acid gives methyl 4-formylbenzoate (VI), which is condensed with nitroethane by means of butylamine and acetic acid in benzene to give methyl 4-(2-nitro-1-propenyl)benzoate (VII). The treatment of (VII) with Fe and HCl in refluxing methanol yields methyl 4-(acetonyl)benzoate (VIII), which is reductocondensed with (R*)-2-amino-1-phenylethanol (IX) by means of NaBH4 in refluxing benzene and crystallized in methanol to fractionate the optical diastereomers. Finally, the (R*,R*)-isomer (X) is treated with fumaric acid.

1 Freer, R.; Morecombe, D.J.; The synthesis of [14C]BRL 26830A, a novel beta-adrenoceptor agonist. J Label Compd Radiopharm 1992, 31, 9, 697.
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
23808 Fumaric acid; (E)-2-butenedioic acid 110-17-8 C4H4O4 详情 详情
(IV) 10168 4-Bromobenzoic acid methyl ester; methyl 4-bromobenzoate 619-42-1 C8H7BrO2 详情 详情
(V) 10169 methyl 4-cyanobenzoate;4-Cyanobenzoic acid methyl ester 1129-35-7 C9H7NO2 详情 详情
(V) 44596 methyl 4-cyanobenzoate C9H7NO2 详情 详情
(VI) 10170 methyl 4-formylbenzoate 1571-08-0 C9H8O3 详情 详情
(VI) 44597 methyl 4-formylbenzoate C9H8O3 详情 详情
(VII) 10171 methyl 4-[(Z)-2-nitro-1-propenyl]benzoate C11H11NO4 详情 详情
(VII) 44598 methyl 4-[(Z)-2-nitro-1-propenyl]benzoate C11H11NO4 详情 详情
(VIII) 10172 methyl 4-(2-oxopropyl)benzoate C11H12O3 详情 详情
(VIII) 44599 methyl 4-(2-oxopropyl)benzoate C11H12O3 详情 详情
(IX) 10173 (1R)-2-Amino-1-phenyl-1-ethanol 2549-14-6 C8H11NO 详情 详情
(X) 44595 methyl 4-((2R)-2-[[(2R)-2-hydroxy-2-phenylethyl]amino]propyl)benzoate C19H23NO3 详情 详情
(X) 44600 methyl 4-((2R)-2-[[(2R)-2-hydroxy-2-phenylethyl]amino]propyl)benzoate C19H23NO3 详情 详情
Extended Information