ethyl (4R)-3-[2-(2,3-dihydro-1H-inden-2-yl)acetyl]-1,3-thiazolidine-4-carboxylate -Drug Synthesis Database

【结构式】

【分子编号】55612

【品名】ethyl (4R)-3-[2-(2,3-dihydro-1H-inden-2-yl)acetyl]-1,3-thiazolidine-4-carboxylate

【CA登记号】

【分子式】C₁₇H₂₁NO₃S

【分子量】319.42468

【元素组成】C 63.92% H 6.63% N 4.38% O 15.03% S 10.04%

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：(II)

The dihydropyridine-4-carboxylic acid derivative (I) was activated as the pentafluorophenyl ester (II) using pentafluorophenol and DCC. Coupling of the active ester (II) with glutamic acid (III) furnished the N-acyl glutamic acid (IV). Alternatively, (IV) was obtained by coupling of glutamic acid (III) with the pyridine acid (I) via activation with DCC/HOBt. Diacid (IV) was finally treated with NaOH to produce the corresponding disodium salt.

参考文献中间体

合成目标

【1】 Biseniex, E.A.; Uldrikis, Y.R.; Dubur, G.Y.; Veveris, M.M.; Kimenis, A.A.; Ivanov, E.V. (Latvian Institute of Organic Synthesis); 2-(2,6-Dimethyl-3,5-diethoxycarbonyl-1,4-dihydropyridine-4-carboxamide) glutaric acid its disodium salt and method of their preparation. US 4485239 .

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)	55616	3,5-bis(ethoxycarbonyl)-2,6-dimethyl-1,4-dihydro-4-pyridinecarboxylic acid		C₁₄H₁₉NO₆	详情	详情
(II)	55612	ethyl (4R)-3-[2-(2,3-dihydro-1H-inden-2-yl)acetyl]-1,3-thiazolidine-4-carboxylate		C₁₇H₂₁NO₃S	详情	详情
(III)	12005	L-2-Amino propane dicarboxylic acid; (-)-2-Aminoglutaric acid; L-2-Aminopentanoic acid; L-Glutamic acid	56-86-0	C₅H₉NO₄	详情	详情
(IV)	55618	(2S)-2-({[3,5-bis(ethoxycarbonyl)-2,6-dimethyl-1,4-dihydro-4-pyridinyl]carbonyl}amino)pentanedioic acid		C₁₉H₂₆N₂O₉	详情	详情

合成路线2

该中间体在本合成路线中的序号：(VI)

Coupling of indanylacetic acid (IV) with L-thioproline ethyl ester (V) by means of EDC gave amide (VI). Subsequent saponification of the ethyl ester group of (VI) furnished (indanylacetyl)thioproline (VII). The title compound was finally obtained by coupling of acid (VII) with pyrrolidine (VIII).

参考文献中间体

合成目标

【1】 Aotsuka, T.; Torizuka, M.; Soeda, M.; Ogura, K.; Tanaka, Y.; Kato, H.; Nakata, N.; Miura, N.; Morita, H. (Zeria Pharmaceutical Co., Ltd.); Condensed benzene deriv.. AU 8945914; EP 0372484; JP 1990262557; US 5028604 .

中间体序号	中间体编号	品名	CAS号	分子式	供应商	用于合成
(IV)	21721	2-(2,3-dihydro-1H-inden-2-yl)acetic acid	37868-26-1	C₁₁H₁₂O₂	详情	详情
(V)	12901	ethyl (4R)-1,3-thiazolidine-4-carboxylate		C₆H₁₁NO₂S	详情	详情
(VI)	55612	ethyl (4R)-3-[2-(2,3-dihydro-1H-inden-2-yl)acetyl]-1,3-thiazolidine-4-carboxylate		C₁₇H₂₁NO₃S	详情	详情
(VII)	55613	(4R)-3-[2-(2,3-dihydro-1H-inden-2-yl)acetyl]-1,3-thiazolidine-4-carboxylic acid		C₁₅H₁₇NO₃S	详情	详情
(VIII)	11376	Pyrrolidine	123-75-1	C₄H₉N	详情	详情

Extended Information