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

【结 构 式】

【分子编号】18478

【品名】tert-butyl 2-([(1R)-1-[(4-[2-[(isopropylsulfonyl)amino]phenyl]-1-piperazinyl)carbonyl]-4-phenylbutyl]amino)-1,1-dimethyl-2-oxoethylcarbamate

【CA登记号】

【 分 子 式 】C33H49N5O6S

【 分 子 量 】643.84816

【元素组成】C 61.56% H 7.67% N 10.88% O 14.91% S 4.98%

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:(XI)

N-Boc-D-(3-phenylpropyl)glycine (I) was esterified to benzyl ester (II), and then, tert-butoxycarbonyl group was cleaved by acidic treatment to give amine (III). This was coupled with N-Boc-2-aminoisobutyric acid (IV) in the presence of 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide.HCl (EDC) and 1-hydroxybenzotriazole (HOBt) to afford dipeptide ester (V), from which the benzyl ester group was removed by hydrogenolysis in the presence of Pd/C. The resulting acid (VI) was condensed with 1-(2-nitrophenyl)piperazine (VII) in the presence of EDC and HOBt to produce piperazide (VIII). Subsequent reduction of the nitro group by hydrogenation in the presence of Raney-Ni gave aniline (IX), which was treated with 2-propanesulfonyl chloride (X) to yield sulfonamide (XI). Finally, the tert-butoxycarbonyl protecting group was removed by treatment either with HCl in EtOAc or with trifluoroacetic acid to afford the target compound as the hydrochloride or the trifluoroacetate salt, respectively.

1 Barakat, K.J.; Cheng, K.; Chan, W.W.; Butler, B.S.; Jacks, T.M.; Schleim, K.D.; Hora, D.F. Jr.; Hickey, G.J.; Smith, R.G.; Patchett, A.A.; Nargund, R.P.; Synthesis and biological activities of phenyl piperazine-based peptidomimetic growth hormone secretagogues. Bioorg Med Chem Lett 1998, 8, 11, 1431.
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) 18468 (2R)-2-[(tert-butoxycarbonyl)amino]-5-phenylpentanoic acid C16H23NO4 详情 详情
(II) 18469 benzyl (2R)-2-[(tert-butoxycarbonyl)amino]-5-phenylpentanoate C23H29NO4 详情 详情
(III) 18470 benzyl (2R)-2-amino-5-phenylpentanoate C18H21NO2 详情 详情
(IV) 18471 N-(tert-butoxycarbonyl)-2-methylalanine 30992-29-1 C9H17NO4 详情 详情
(V) 18472 benzyl (2R)-2-([2-[(tert-butoxycarbonyl)amino]-2-methylpropanoyl]amino)-5-phenylpentanoate C27H36N2O5 详情 详情
(VI) 18473 (2R)-2-([2-[(tert-butoxycarbonyl)amino]-2-methylpropanoyl]amino)-5-phenylpentanoic acid C20H30N2O5 详情 详情
(VII) 18474 1-(2-nitrophenyl)piperazine C10H13N3O2 详情 详情
(VIII) 18475 tert-butyl 1,1-dimethyl-2-[((1R)-1-[[4-(2-nitrophenyl)-1-piperazinyl]carbonyl]-4-phenylbutyl)amino]-2-oxoethylcarbamate C30H41N5O6 详情 详情
(IX) 18476 tert-butyl 2-[((1R)-1-[[4-(2-aminophenyl)-1-piperazinyl]carbonyl]-4-phenylbutyl)amino]-1,1-dimethyl-2-oxoethylcarbamate C30H43N5O4 详情 详情
(X) 18477 2-propanesulfonyl chloride 10147-37-2 C3H7ClO2S 详情 详情
(XI) 18478 tert-butyl 2-([(1R)-1-[(4-[2-[(isopropylsulfonyl)amino]phenyl]-1-piperazinyl)carbonyl]-4-phenylbutyl]amino)-1,1-dimethyl-2-oxoethylcarbamate C33H49N5O6S 详情 详情
Extended Information