1-isocyanatoadamantane; 1-adamantyl isocyanate -Drug Synthesis Database

【结构式】

【分子编号】47210

【品名】1-isocyanatoadamantane; 1-adamantyl isocyanate

【CA登记号】4411-25-0

【分子式】C₁₁H₁₅NO

【分子量】177.24624

【元素组成】C 74.54% H 8.53% N 7.9% O 9.03%

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：(V)

Guanidilation of substituted aniline (I) with protected guanidine (II) provides derivative (III), whose Boc group is removed by treatment with TFA or HCl to afford (4-aminomethyl)phenyl-2,3-di(benzyloxycarbonyl)guanidine (IV). Finally, the target product is obtained by coupling of (IV) with 1-adamantyl-isocyanate (V), followed by removal of the protecting group by hydrogenation over Pd/C.

参考文献中间体

合成目标

【2】 Magdolen, V.; Moroder, L.; Sperl, S.; Sturzebecher, J.; Wilhelm, O. (Wilex Biotechnology GmbH); Selective inhibitors of the urokinase plasminogene activators. DE 19940389; WO 0114324 .
【1】 Stürzebecher, J.; Jacob, U.; Magdolen, V.; Huber, R.; Wilhelm, O.G.; Sperl, S.; Moroder, L.; Bode, W.; Arroyo de Prada, N.; (4-Aminomethyl)phenylguanidine derivatives as nonpeptidic highly selective inhibitors of human urokinase. Proceedings of the National Academy of Sciences of the United States of America 2000, 97, 10, 5113.

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)	35549	tert-butyl 4-aminobenzylcarbamate		C₁₂H₁₈N₂O₂	详情	详情
(II)	47207	benzyl [[(benzyloxy)carbonyl]amino][[(trifluoromethyl)sulfonyl]imino]methylcarbamate		C₁₈H₁₆F₃N₃O₆S	详情	详情
(III)	47208	benzyl (Z)-[[(benzyloxy)carbonyl]amino](4-[[(tert-butoxycarbonyl)amino]methyl]anilino)methylidenecarbamate		C₂₉H₃₂N₄O₆	详情	详情
(IV)	47209	benzyl (Z)-[4-(aminomethyl)anilino][[(benzyloxy)carbonyl]amino]methylidenecarbamate		C₂₄H₂₄N₄O₄	详情	详情
(V)	47210	1-isocyanatoadamantane; 1-adamantyl isocyanate	4411-25-0	C₁₁H₁₅NO	详情	详情
(VI)	47211	benzyl (Z)-[4-([[(1-adamantylamino)carbonyl]amino]methyl)anilino][[(benzyloxy)carbonyl]amino]methylidenecarbamate		C₃₅H₃₉N₅O₅	详情	详情

Extended Information