N-[1-(Methanesulfonyl)spiro[indoline-3,4'-piperidin]-1'-ylcarbonyl]-L-tryptophan -Drug Synthesis Database

【结构式】

【分子编号】25799

【品名】N-[1-(Methanesulfonyl)spiro[indoline-3,4'-piperidin]-1'-ylcarbonyl]-L-tryptophan

【CA登记号】

【分子式】C₂₅H₂₈N₄O₅S

【分子量】496.58728

【元素组成】C 60.47% H 5.68% N 11.28% O 16.11% S 6.46%

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：(VIII)

The compound can be prepared by two related ways. Coupling of N-Boc-L-tryptophan (I) with benzyl methyl amine (II) employing EDC and HOBt afforded amide (III). The Boc group of (III) was removed by treatment with trifluoroacetic acid and anisole to give amine (IV). Then, sequential reaction of (IV) with 1,1'-carbonyldiimidazole and with piperidine (V) yielded the target urea. In a related procedure, urea formation between L-tryptophan benzyl ester (VI) and piperidine (V) gave (VII). Subsequent catalytic hydrogenolysis of the benzyl ester of (VII) provided acid (VIII). This was finally coupled to benzyl methyl amine (II) to produce the title compound.

参考文献中间体

合成目标

【1】 Qi, S.; Shah, S.K.; Cascieri, M.A.; Sadowski, S.J.; MaCcoss, M.; L-tryptophan urea amides as NK1/NK2 dual antagonists. Bioorg Med Chem Lett 1998, 8, 16, 2259.

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)	16114	N-alpha-t-BOC-L-tryptophan; (2S)-2-[(tert-butoxycarbonyl)amino]-3-(1H-indol-3-yl)propionic acid	13139-14-5	C₁₆H₂₀N₂O₄	详情	详情
(III)	25794	tert-butyl (1S)-2-[benzyl(methyl)amino]-1-(1H-indol-3-ylmethyl)-2-oxoethylcarbamate		C₂₄H₂₉N₃O₃	详情	详情
(IV)	25795	(2S)-2-amino-N-benzyl-3-(1H-indol-3-yl)-N-methylpropanamide		C₁₉H₂₁N₃O	详情	详情
(V)	25796	1-(Methylsulfonyl)spiro[indoline-3,4'-piperidine]		C₁₃H₁₈N₂O₂S	详情	详情
(VI)	25797	benzyl (2S)-2-amino-3-(1H-indol-3-yl)propanoate		C₁₈H₁₈N₂O₂	详情	详情
(VII)	25798	N-[1-(Methanesulfonyl)spiro[indoline-3,4'-piperidin]-1'-ylcarbonyl]-L-tryptophan benzyl ester		C₃₂H₃₄N₄O₅S	详情	详情
(VIII)	25799	N-[1-(Methanesulfonyl)spiro[indoline-3,4'-piperidin]-1'-ylcarbonyl]-L-tryptophan		C₂₅H₂₈N₄O₅S	详情	详情

Extended Information