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【结 构 式】

【分子编号】28327

【品名】ethyl 3,3-dimethyl-5-[5-[2-(4-methylphenyl)acetyl]-2-thienyl]pentanoate

【CA登记号】

【 分 子 式 】C22H28O3S

【 分 子 量 】372.52852

【元素组成】C 70.93% H 7.58% O 12.88% S 8.61%

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:(XVI)

The reaction of 3,3-dimethylglutaric acid monomethyl ester (XI) with SOCl2 in dichloromethane gives the monoacyl chloride (XII), which is condensed with thiophene (III), by means of SnCl4 in dichloromethane yielding the 5-oxopentanoic ester (XIII). The reduction and simultaneous hydrolysis of (XIII) with hydrazine and KOH affords the pentanoic acid (XIV), which is reesterified with ethanol and sulfuric acid to the ester (XV). The condensation of (XV) with the previously described 2-phenylacetyl chloride (II) by means of SnCl4 in dichloromethane gives the ethanone derivative (XVI), which is reduced with hydrazine and KOH to the previously described pentanoic acid (VIII). Its condensation with piperazine (IX) to afford (X) and the final reduction to the target compound have already been described.

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
(II) 21017 2-(4-methylphenyl)acetyl chloride 35675-44-6 C9H9ClO 详情 详情
(III) 13297 Thiophene 110-02-1 C4H4S 详情 详情
(VIII) 28320 3,3-dimethyl-5-[5-(4-methylphenethyl)-2-thienyl]pentanoic acid C20H26O2S 详情 详情
(IX) 24354 2,3-dimethoxy-4-(1-piperazinylmethyl)phenyl methyl ether C14H22N2O3 详情 详情
(X) 28321 3,3-dimethyl-5-[5-(4-methylphenethyl)-2-thienyl]-1-[4-(2,3,4-trimethoxybenzyl)-1-piperazinyl]-1-pentanone C34H46N2O4S 详情 详情
(XI) 28322 5-methoxy-3,3-dimethyl-5-oxopentanoic acid C8H14O4 详情 详情
(XII) 28323 methyl 5-chloro-3,3-dimethyl-5-oxopentanoate C8H13ClO3 详情 详情
(XIII) 28324 methyl 3,3-dimethyl-5-oxo-5-(2-thienyl)pentanoate C12H16O3S 详情 详情
(XIV) 28325 3,3-dimethyl-5-(2-thienyl)pentanoic acid C11H16O2S 详情 详情
(XV) 28326 ethyl 3,3-dimethyl-5-(2-thienyl)pentanoate C13H20O2S 详情 详情
(XVI) 28327 ethyl 3,3-dimethyl-5-[5-[2-(4-methylphenyl)acetyl]-2-thienyl]pentanoate C22H28O3S 详情 详情
Extended Information