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【结 构 式】

【分子编号】45619

【品名】benzyl 3-[[(1-ethyl-1H-pyrrol-2-yl)carbonyl]amino]propanoate

【CA登记号】

【 分 子 式 】C17H20N2O3

【 分 子 量 】300.35748

【元素组成】C 67.98% H 6.71% N 9.33% O 15.98%

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:(VI)

Treatment of methyl pyrrole-2-carboxylate (I) with KOtBu and 18-crown-6 in Et2O, followed by reaction with ethyl iodide (II) in Et2O, yields methyl 1-ethylpyrrole-2-carboxylate (III), which is then subjected to saponification with NaOH to afford carboxylic acid (IV). Condensation of (IV) with beta-alanine benzyl ester p-toluene sulfonate (V) in the presence of diethyl phosphorocyanidate (DEPC) and Et3N in DMF provides benzyl ester (VI), which is then hydrogenated over Pd/C in THF, furnishing carboxylic acid (VII). Cyclization of (VII) with polyphosphoric acid (PPA) affords derivative (VIII), which is then treated with NaH in DMF and alkylated with chloro derivative (IX) in DMF to produce compound (X). Finally, treatment of (X) with hydroxylamine hydrochloride and NaOAc affords the target compound.

1 Mizuno, A.; Miya, M.; Inomata, N.; Tatsuoka, T.; Ishihara, T. (Suntory Ltd.); Pyrroloazepine cpd.. EP 0557526; JP 1993503481; US 5399557; WO 9303032 .
2 Yamaki, A.; Tatsuoka, T.; Miya, M.; Nakanishi, K.; Mizuno, A.; Takiguchi, C.; Hidaka, T.; Kamei, T.; Shibata, M.; Inomata, N.; Studies on antihypertensive agents with antithrombotic activity. 2. Syntheses and pharmacological evaluation of pyrrolo[2,3-c]azepine derivatives. Chem Pharm Bull 2000, 48, 8, 1129.
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) 45616 methyl 1H-pyrrole-2-carboxylate C6H7NO2 详情 详情
(II) 10925 Iodoethane;ethyl iod 75-03-6 C2H5I 详情 详情
(III) 45617 methyl 1-ethyl-1H-pyrrole-2-carboxylate C8H11NO2 详情 详情
(IV) 45618 1-ethyl-1H-pyrrole-2-carboxylic acid C7H9NO2 详情 详情
(V) 30194 benzyl 3-aminopropanoate 27019-47-2 C10H13NO2 详情 详情
(VI) 45619 benzyl 3-[[(1-ethyl-1H-pyrrol-2-yl)carbonyl]amino]propanoate C17H20N2O3 详情 详情
(VII) 45620 N-[(1-ethyl-1H-pyrrol-2-yl)carbonyl]-beta-alanine C10H14N2O3 详情 详情
(VIII) 45621 1-ethyl-6,7-dihydropyrrolo[2,3-c]azepine-4,8(1H,5H)-dione C10H12N2O2 详情 详情
(IX) 45622 1-(3-chloropropyl)-4-(4-fluorophenyl)piperazine C13H18ClFN2 详情 详情
(X) 45623 1-ethyl-7-[3-[4-(4-fluorophenyl)-1-piperazinyl]propyl]-6,7-dihydropyrrolo[2,3-c]azepine-4,8(1H,5H)-dione C23H29FN4O2 详情 详情
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