【结 构 式】 |
【分子编号】29384 【品名】(2R)-3-(tert-butoxy)-2-[(isobutoxycarbonyl)amino]propionic acid 【CA登记号】 |
【 分 子 式 】C12H23NO5 【 分 子 量 】261.31836 【元素组成】C 55.16% H 8.87% N 5.36% O 30.61% |
合成路线1
该中间体在本合成路线中的序号:(XIV)The compound was also prepared by solution-phase synthesis. Treatment of O-tert-butyl-D-serine (XIII) with isobutyl chloroformate (XII) produced carbamate (XIV). Subsequent coupling of (XIV) with L-alanine tert-butyl ester (XV) by means of EDC and HOBt yielded the protected dipeptide (XVI). Deprotection of both tert-butyl groups of (XVI) with trifluoroacetic acid produced dipeptide (XVII), which was coupled to nitro-L-arginine ethyl aminal (XVIII) to furnish tripeptide (XIX). Hydrogenolysis of the nitro group of (XIX) over Pd/C gave (XX). The ethyl acetal of (XX) was finally hydrolyzed in 3M HCl to yield the title compound.
【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 |
---|---|---|---|---|---|---|
(XII) | 13423 | 1-[(Chlorocarbonyl)oxy]-2-methylpropane; Isobutyl chloroformate;isobutyl carbonochloridate | 543-27-1 | C5H9ClO2 | 详情 | 详情 |
(XIII) | 29383 | (2R)-2-amino-3-(tert-butoxy)propionic acid | C7H15NO3 | 详情 | 详情 | |
(XIV) | 29384 | (2R)-3-(tert-butoxy)-2-[(isobutoxycarbonyl)amino]propionic acid | C12H23NO5 | 详情 | 详情 | |
(XV) | 29385 | tert-butyl (2S)-2-aminopropanoate | C7H15NO2 | 详情 | 详情 | |
(XVI) | 29386 | tert-butyl (2S)-2-([(2R)-3-(tert-butoxy)-2-[(isobutoxycarbonyl)amino]propanoyl]amino)propanoate | C19H36N2O6 | 详情 | 详情 | |
(XVII) | 29387 | (2S)-2-([(2R)-3-hydroxy-2-[(isobutoxycarbonyl)amino]propanoyl]amino)propionic acid | C11H20N2O6 | 详情 | 详情 | |
(XVIII) | 29388 | 3(S)-Amino-2-ethoxy-N2-nitropiperidine-1-carboxamidine | C8H17N5O3 | 详情 | 详情 | |
(XIX) | 29389 | Isobutoxycarbinyl-D-seryl-L-alanine 1-[2-ethoxy-1-(N2-nitroamidino)piperidin-3(S)-ylamide | C19H35N7O8 | 详情 | 详情 | |
(XX) | 29390 | isobutyl (1R)-2-[[(1S)-2-([(3S)-1-[amino(imino)methyl]-2-ethoxypiperidinyl]amino)-1-methyl-2-oxoethyl]amino]-1-(hydroxymethyl)-2-oxoethylcarbamate | C19H36N6O6 | 详情 | 详情 |