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

【结 构 式】

【分子编号】10349

【品名】ethyl (2S)-2-amino-3-(1H-indol-3-yl)propanoate

【CA登记号】

【 分 子 式 】C13H16N2O2

【 分 子 量 】232.28232

【元素组成】C 67.22% H 6.94% N 12.06% O 13.78%

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)

This compound can be obtained by two related ways: 1) The reaction of vinblastine (I) with anhydrous hydrazine in hot ethanol gives 4-deacetylvinblastine-23-acid hydrazide (II), which by reaction with HCl and NaNO2 in cool methanol - water is converted into the corresponding azide (III). Finally, this compound is condensed with L-tryptophan ethyl ester (IV) in dichloromethane. 2) The hydrolysis of vinblastine (I) with NaOH in refluxing ethanol gives 4-deacetylvinblastoic acid (V), which is condensed with L-tryptophan ethyl ester (IV) by means of isobutyl chloroformate (VI) and N-ethylmorpholine in DMF to afford the 4-O-(isobutoxycarbonyl) derivative (VII). Finally, this compound is partially hydrolyzed with KOH in ethanol.

1 Trouet, A.B.L.; Hannart, J.A.A.J.; Rao, K.S.B. (OmniChem); Vinblastin-23-oyl amino acid derivs. US 4639456 .
2 Hamashima, Y. (Shionogi & Co. Ltd.); 7-Carboxyalkenoylamido-3-cephem-4-carboxylic acid derivs.. EP 0136721; ES 8604602; ES 8605278; ES 8700222; GB 2154580; GB 2198727; JP 1985078987; JP 1985163884; JP 1985246388; US 4634697; US 4748170 .
3 Trouet, A.B.L.; Rao, K.S.B.; Hannart, J.A.A. (OmniChem); N-Vinblastinoyl-23) derivs. of amino acids and peptides, their preparation and their therapeutic application. EP 0041935 .
4 Atassi, G.; Rao, K.S.P.B.; Collard, M.-P.M.; Trouet, A.; Dejonghe, J.P.C.; Hannart, J.A.; Vinblastin-23-oyl amino acid derivatives: Chemistry, physicochemical data, toxicity, and antitumor activities against P388 and L1210 leukemias. J Med Chem 1985, 28, 8, 1079.
5 Castaner, J.; Prous, J.; Vintriptol Mesylate. Drugs Fut 1992, 17, 7, 569.
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) 10346 methyl (3aR,4R,5S,5aR,10bR,13aR)-4-(acetoxy)-3a-ethyl-9-[(13S,15S,17S)-17-ethyl-17-hydroxy-13-(methoxycarbonyl)-1,11-diazatetracyclo[13.3.1.0(4,12).0(5,10)]nonadeca-4(12),5,7,9-tetraen-13-yl]-5-hydroxy-8-methoxy-6-methyl-3a,4,5,5a,6,11,12,13a-octahydro-1H-indolizino[8,1-cd]carbazole-5-carboxylate 446-86-6 C46H58N4O9 详情 详情
(II) 10347 methyl (13S,15S,17S)-13-[(3aR,4R,5S,5aR,10bR,13aR)-3a-ethyl-5-(hydrazinocarbonyl)-4,5-dihydroxy-8-methoxy-6-methyl-3a,4,5,5a,6,11,12,13a-octahydro-1H-indolizino[8,1-cd]carbazol-9-yl]-17-ethyl-17-hydroxy-1,11-diazatetracyclo[13.3.1.0(4,12).0(5,10)]nonadeca-4(12),5,7,9-tetraene-13-carboxylate C43H56N6O7 详情 详情
(III) 10348 1-([(3aR,4R,5S,5aR,10bR,13aR)-3a-Ethyl-9-[(13S,15S,17S)-17-ethyl-17-hydroxy-13-(methoxycarbonyl)-1,11-diazatetracyclo[13.3.1.0(4,12).0(5,10)]nonadeca-4(12),5,7,9-tetraen-13-yl]-4,5-dihydroxy-8-methoxy-6-methyl-3a,4,5,5a,6,11,12,13a-octahydro-1H-indolizino[8,1-cd]carbazol-5-yl]carbonyl)-1,2-triazadien-2-ium C43H53N7O7 详情 详情
(IV) 10349 ethyl (2S)-2-amino-3-(1H-indol-3-yl)propanoate C13H16N2O2 详情 详情
(V) 10350 (3aR,4R,5S,5aR,10bR,13aR)-3a-Ethyl-9-[(13S,15S,17S)-17-ethyl-17-hydroxy-13-(methoxycarbonyl)-1,11-diazatetracyclo[13.3.1.0(4,12).0(5,10)]nonadeca-4(12),5,7,9-tetraen-13-yl]-4,5-dihydroxy-8-methoxy-6-methyl-3a,4,5,5a,6,11,12,13a-octahydro-1H-indolizino[8,1-cd]carbazole-5-carboxylic acid C43H54N4O8 详情 详情
(VI) 13423 1-[(Chlorocarbonyl)oxy]-2-methylpropane; Isobutyl chloroformate;isobutyl carbonochloridate 543-27-1 C5H9ClO2 详情 详情
(VII) 10351 methyl (13S,15S,17S)-13-[(3aR,4R,5S,5aR,10bR,13aR)-5-([[(1S)-2-ethoxy-1-(1H-indol-3-ylmethyl)-2-oxoethyl]amino]carbonyl)-3a-ethyl-5-hydroxy-4-[(isobutoxycarbonyl)oxy]-8-methoxy-6-methyl-3a,4,5,5a,6,11,12,13a-octahydro-1H-indolizino[8,1-cd]carbazol-9-yl]-17-ethyl-17-hydroxy-1,11-diazatetracyclo[13.3.1.0(4,12).0(5,10)]nonadeca-4(12),5,7,9-tetraene-13-carboxylate C61H76N6O11 详情 详情
Extended Information