• English
  • 简体中文
Login Register
Current Location: Home > Feedback Help Print

【结 构 式】

【分子编号】42994

【品名】12-ethyl 8-methyl (8S)-3,10-dioxo-1-phenyl-2-oxa-4,9,11-triazadodecane-8,12-dicarboxylate

【CA登记号】

【 分 子 式 】C19H27N3O7

【 分 子 量 】409.4394

【元素组成】C 55.74% H 6.65% N 10.26% O 27.35%

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:(IV)

Conversion of amino acid (I) into its methyl ester derivative (II) by means of SOCl2 in MeOH, followed by coupling with ethyl isocyanatoacetate (III) and Et3N in CH2Cl2/THF yields derivative (IV). Cyclization of (IV) by means of H2O/HCl affords hydantoin (V), which reacts with 2-methylthio-2-imidazoline (VI) in an aqueous NaOH solution to provide cyclic guanidine derivative (VII). Treatment of amino acid (VIII) with isobutylene (IX) and H2SO4 in dioxane affords t-Bu ester (X), which then couples with (VII) by means of HOBt and DCC in DMF to furnish derivative (XI). Finally, tert-butyl ester is hydrolyzed by treatment with TFA in the presence of 1,2-dimercaptoethane.

1 Knolle, J.; Peyman, A.; Wehner, V.; et al.; RGD mimetics containing a central hydantoin scaffold: alphavbeta3 vs alphaIIbbeta3 selective requirements. Bioorg Med Chem Lett 2000, 10, 2, 179.
2 Wehner, V.; Knolle, J.; Stilz, H.U.; Carniato, D.; Gourvest, J.-F.; Gadek, T.; McDowell, R. (Aventis SA); Inhibitors of bone resorption and vitronectin receptor antagonists. DE 19626701; DE 19635522; EP 0796855 .
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) 30898 (2S)-2-amino-5-[[(benzyloxy)carbonyl]amino]pentanoic acid C13H18N2O4 详情 详情
(II) 42993 methyl (2S)-2-amino-5-[[(benzyloxy)carbonyl]amino]pentanoate C14H20N2O4 详情 详情
(III) 18312 ETHYL ISOCYANATOACETATE; ethyl 2-isocyanatoacetate 2949-22-6 C5H7NO3 详情 详情
(IV) 42994 12-ethyl 8-methyl (8S)-3,10-dioxo-1-phenyl-2-oxa-4,9,11-triazadodecane-8,12-dicarboxylate C19H27N3O7 详情 详情
(V) 42295 (2R)-N-methyl-2-(methylamino)-3-(2-naphthyl)-N-[(1R)-2-oxo-1-(2-thienylmethyl)-2-(1,2,2-trimethylhydrazino)ethyl]propanamide C25H32N4O2S 详情 详情
(VI) 42996 4,5-dihydro-1H-imidazol-2-yl methyl sulfide; 2-(methylsulfanyl)-4,5-dihydro-1H-imidazole 5464-11-9 C4H8N2S 详情 详情
(VII) 42997 2-[(4S)-4-[3-(4,5-dihydro-1H-imidazol-2-ylamino)propyl]-2,5-dioxoimidazolidinyl]acetic acid C11H17N5O4 详情 详情
(VIII) 18008 (2S)-3-amino-2-[[(benzyloxy)carbonyl]amino]propionic acid; N(alpha)-Z-L-2,3-diaminopropionic acid 35761-26-3 C11H14N2O4 详情 详情
(IX) 15926 2-methyl-1-propene; isobutylene 115-11-7 C4H8 详情 详情
(X) 18009 tert-butyl (2S)-3-amino-2-[[(benzyloxy)carbonyl]amino]propanoate C15H22N2O4 详情 详情
(XI) 42998 tert-butyl (2S)-2-[[(benzyloxy)carbonyl]amino]-3-[(2-[(4S)-4-[3-(4,5-dihydro-1H-imidazol-2-ylamino)propyl]-2,5-dioxoimidazolidinyl]acetyl)amino]propanoate C26H37N7O7 详情 详情
Extended Information