tert-butyl (2S)-6-[[(benzyloxy)carbonyl]amino]-2-[[(2R,3S)-3-(1H-indol-3-yl)-2-([[4-(2-oxo-2,3-dihydro-1H-benzimidazol-1-yl)-1-piperidinyl]carbonyl]amino)butanoyl]amino]hexanoate -Drug Synthesis Database

【结构式】

【分子编号】28258

【品名】tert-butyl (2S)-6-[[(benzyloxy)carbonyl]amino]-2-[[(2R,3S)-3-(1H-indol-3-yl)-2-([[4-(2-oxo-2,3-dihydro-1H-benzimidazol-1-yl)-1-piperidinyl]carbonyl]amino)butanoyl]amino]hexanoate

【CA登记号】

【分子式】C₄₃H₅₃N₇O₇

【分子量】779.9368

【元素组成】C 66.22% H 6.85% N 12.57% O 14.36%

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：(VI)

Coupling of N-Boc-beta-methyltryptophan (I) with N-Cbz-lysine tert-butyl ester (II) using EDC and HOBt afforded dipeptide (III). Selective deprotection of the Boc group of (III) with methanesulfonic acid gave amine (IV). This was converted to urea (VI) upon treatment with benzimidazolylpiperidine (V) and N,N'-disuccinimidyl carbonate in the presence of diisopropyl ethylamine. The N-carbobenzoxy group of (VI) was finally deprotected by hydrogenolysis over Pd/C.

参考文献中间体

合成目标

【1】 Synthesis and biological activities of potent peptidomimetics selective for somatostatin receptor subtype 2. Proc Natl Acad Sci USA 1998, 95, 18, 10836.
【2】 Berk, S.; Yang, L.; Chen, M.H.; Johnston, D.; Pasternak, A.; Chapman, K.; Guo, L.; Nargund, R.; Tata, J.R.; Patchett, A.A. (Merck & Co., Inc.); Somatostatin agonists. EP 0984779; US 6063796; WO 9844922 .

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)	28255	(2R,3S)-2-[(tert-butoxycarbonyl)amino]-3-(1H-indol-3-yl)butyric acid		C₁₇H₂₂N₂O₄	详情	详情
(II)	21879	tert-butyl (2S)-2-amino-6-[[(benzyloxy)carbonyl]amino]hexanoate		C₁₈H₂₈N₂O₄	详情	详情
(III)	28256	tert-butyl (2S)-6-[[(benzyloxy)carbonyl]amino]-2-[[(2R,3S)-2-[(tert-butoxycarbonyl)amino]-3-(1H-indol-3-yl)butanoyl]amino]hexanoate		C₃₅H₄₈N₄O₇	详情	详情
(IV)	28257	tert-butyl (2S)-2-[[(2R,3S)-2-amino-3-(1H-indol-3-yl)butanoyl]amino]-6-[[(benzyloxy)carbonyl]amino]hexanoate		C₃₀H₄₀N₄O₅	详情	详情
(V)	12138	1-(4-Piperidinyl)-1,3-dihydro-2H-benzimidazol-2-one; 4-(2-Keto-1-benzimidazolinyl)piperidine	20662-53-7	C₁₂H₁₅N₃O	详情	详情
(VI)	28258	tert-butyl (2S)-6-[[(benzyloxy)carbonyl]amino]-2-[[(2R,3S)-3-(1H-indol-3-yl)-2-([[4-(2-oxo-2,3-dihydro-1H-benzimidazol-1-yl)-1-piperidinyl]carbonyl]amino)butanoyl]amino]hexanoate		C₄₃H₅₃N₇O₇	详情	详情

Extended Information