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【结 构 式】

【分子编号】29378

【品名】ethyl 6-([(3S)-1-[[[(allyloxy)carbonyl]imino](amino)methyl]-3-[(tert-butoxycarbonyl)amino]piperidinyl]oxy)hexanoate

【CA登记号】

【 分 子 式 】C23H40N4O7

【 分 子 量 】484.59336

【元素组成】C 57.01% H 8.32% N 11.56% O 23.11%

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:(VII)

The title compound has been prepared by either solid-phase or solution-phase synthesis. In the first case, N(alpha)-Boc-N(omega)-nitro-L-arginine (I) was coupled with N,O-dimethylhydroxylamine, and the resulting N-methoxy-amide (II) was reduced with LiAlH4 to the corresponding aldehyde, isolated as the cyclic hemiaminal (III). Deprotection of the N-nitro group of (III) by hydrogenation over Pd/C afforded guanidine (IV), which was condensed with allyl chloroformate to give the allyl carbamate (V). Subsequent acid-catalyzed condensation with ethyl 6-hydroxyhexanoate (VI) at the aminal hydroxyl group provided ketal (VII). After hydrolysis of the ethyl ester of (VII), the resulting carboxylic acid (VIII) was coupled to amino-resin to produce the amide-resin (IX).

1 Cohen, C.R.; Weinhouse, M.I.; Roberts, C.; et al.; Synthesis and biological activity of transition-state urokinase inhibitors. 217th ACS Natl Meet (March 21 1999, Anaheim) 1999, Abst MEDI 090.
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
38115 3-[(chlorocarbonyl)oxy]-1-propene 2937-50-0 C4H5ClO2 详情 详情
(I) 29372 N-alpha-(tert-butoxycarbonyl)-N-omega'-nitro-L-arginine C11H21N5O6 详情 详情
(II) 29373 N-alpha-(tert-butoxycarbonyl)-N1-methoxy-N1-methyl-N-omega'-nitro-L-argininamide C13H26N6O6 详情 详情
(III) 29374 3(S)-(Tert-butoxycarbonylamino)-2-hydroxy-N2-nitropiperidine-1-carboxamidine C11H21N5O5 详情 详情
(IV) 29375 tert-butyl (3S)-1-[amino(imino)methyl]-2-hydroxypiperidinylcarbamate C11H22N4O3 详情 详情
(V) 29376 allyl (E)-amino[(3S)-3-[(tert-butoxycarbonyl)amino]-2-hydroxypiperidinyl]methylidenecarbamate C15H26N4O5 详情 详情
(VI) 29377 ethyl 6-hydroxyhexanoate C8H16O3 详情 详情
(VII) 29378 ethyl 6-([(3S)-1-[[[(allyloxy)carbonyl]imino](amino)methyl]-3-[(tert-butoxycarbonyl)amino]piperidinyl]oxy)hexanoate C23H40N4O7 详情 详情
(VIII) 29379 6-([(3S)-1-[[[(allyloxy)carbonyl]imino](amino)methyl]-3-[(tert-butoxycarbonyl)amino]piperidinyl]oxy)hexanoic acid C21H36N4O7 详情 详情
(IX) 29380 allyl (E)-amino[(3S)-2-[(6-amino-6-oxohexyl)oxy]-3-[(tert-butoxycarbonyl)amino]piperidinyl]methylidenecarbamate C21H37N5O6 详情 详情
Extended Information