1-(tert-butoxycarbonyl)-2-indolinecarboxylic acid -Drug Synthesis Database

【结构式】

【分子编号】61011

【品名】1-(tert-butoxycarbonyl)-2-indolinecarboxylic acid

【CA登记号】

【分子式】C₁₄H₁₇NO₄

【分子量】263.29332

【元素组成】C 63.87% H 6.51% N 5.32% O 24.31%

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：(II)

Indoline-2-carboxylic acid (I) is converted into the N-Boc derivative (II) by treatment with Boc2O. Subsequent coupling of (II) with methyl indoline-2-carboxylate (III) by using 2-chloro-1-methylpyridinium iodide (CMPI) provides amide (IV). Hydrolysis of the methyl ester function of (IV) employing LiOH leads to carboxylic acid (V). This is then coupled to N-epsilon-(benzyloxycarbonyl)-lysine methyl ester (VI) in the presence of CMPI to furnish the title compound.

参考文献中间体

合成目标

【1】 Reichert, D.; Kutscher, B.; Bang, H.; Brune, K.; Quinkert, G.; Schaible, H.-G. (Asta Medica AG); Specific immunophilin ligands as antiasthmatics and immunosuppressants. DE 19616509; EP 0896580; JP 2000500776; WO 9741148 .

中间体序号	中间体编号	品名	分子式	供应商	用于合成
(I)	34308	ethyl (2S)-2,3-dihydro-1H-indole-2-carboxylate	C₁₁H₁₃NO₂	详情	详情
(II)	61011	1-(tert-butoxycarbonyl)-2-indolinecarboxylic acid	C₁₄H₁₇NO₄	详情	详情
(III)	61012	methyl 2-indolinecarboxylate	C₁₀H₁₁NO₂	详情	详情
(IV)	61013	tert-butyl 2-{[2-(methoxycarbonyl)-2,3-dihydro-1H-indol-1-yl]carbonyl}-1-indolinecarboxylate	C₂₄H₂₆N₂O₅	详情	详情
(V)	61014	1-{[1-(tert-butoxycarbonyl)-2,3-dihydro-1H-indol-2-yl]carbonyl}-2-indolinecarboxylic acid	C₂₃H₂₄N₂O₅	详情	详情
(VI)	31069	methyl (2S)-2-amino-6-[[(benzyloxy)carbonyl]amino]hexanoate	C₁₅H₂₂N₂O₄	详情	详情

Extended Information