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【结 构 式】

【分子编号】28328

【品名】3-(4-methylphenyl)propionic acid

【CA登记号】1505-50-6

【 分 子 式 】C10H12O2

【 分 子 量 】164.20408

【元素组成】C 73.15% H 7.37% O 19.49%

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:(I)

The reaction of 3-(4-methylphenyl)propionic acid (I) with SOCl2 gives the corresponding acyl chloride (II), which is condensed with thiophene (III) by means SnCl4 yielding 3-(4-methylphenyl)-1-(2-thienyl)propan-1-one (IV). The reduction of (IV) with hydrazine and KOH in hot triethylene glycol affords 2-[3-(4-methylphenyl)propyl]thiophene (V), which is condensed with 3,3-dimethyl glutaric anhydride (VI), by means of AlCl3 in hot nitrobenzene giving the 5-oxopentanoic acid derivative (VII). The reduction of (VII) with hydrazine and KOH as before yields the pentanoic acid derivative (VIII), which is condensed with 4-(2,3,4-trimethoxybenzyl)piperazine (IX) by means of oxalyl chloride to afford the acyl piperazine (X). Finally, the amide group of (X) is reduced with LiAlH4 in ethyl ether.

1 Wierzbicki, M.; et al.; Amino derivatives of phenyl alkyl thiophene as inhibitors of bone resorption. Structure-activity relationship. Arzneim-Forsch Drug Res 1998, 48, 8, 840.
2 Wierzbicki, M.; Sauveur, F.; Bonnet, J.; Brisset, M.; Tordjman, C. (ADIR et Cie.); Thiophene derivs., process for their preparation and pharmaceutical compsns. containing them. AU 9166901; EP 0429370; FR 2655043; JP 1991190872; US 5061704 .
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) 28328 3-(4-methylphenyl)propionic acid 1505-50-6 C10H12O2 详情 详情
(II) 28329 3-(4-methylphenyl)propanoyl chloride C10H11ClO 详情 详情
(III) 13297 Thiophene 110-02-1 C4H4S 详情 详情
(IV) 28330 3-(4-methylphenyl)-1-(2-thienyl)-1-propanone C14H14OS 详情 详情
(V) 28331 2-[3-(4-methylphenyl)propyl]thiophene C14H16S 详情 详情
(VI) 25549 4,4-dimethyldihydro-2H-pyran-2,6(3H)-dione 4160-82-1 C7H10O3 详情 详情
(VII) 28332 3,3-dimethyl-5-[5-[3-(4-methylphenyl)propyl]-2-thienyl]-5-oxopentanoic acid C21H26O3S 详情 详情
(VIII) 28333 3,3-dimethyl-5-[5-[3-(4-methylphenyl)propyl]-2-thienyl]pentanoic acid C21H28O2S 详情 详情
(IX) 24354 2,3-dimethoxy-4-(1-piperazinylmethyl)phenyl methyl ether C14H22N2O3 详情 详情
(X) 28334 3,3-dimethyl-5-[5-[3-(4-methylphenyl)propyl]-2-thienyl]-1-[4-(2,3,4-trimethoxybenzyl)-1-piperazinyl]-1-pentanone C35H48N2O4S 详情 详情
Extended Information