【结 构 式】 |
【分子编号】20399 【品名】N-(Tert-butoxycarbonyl)-L-norleucine isobutoxycarbonyl anhydride 【CA登记号】 |
【 分 子 式 】C16H29NO6 【 分 子 量 】331.4094 【元素组成】C 57.99% H 8.82% N 4.23% O 28.97% |
合成路线1
该中间体在本合成路线中的序号:(II)Mixed anhydride (II), prepared from N-Boc-L-norleucine (I) and isobutyl chloroformate in the presence of Et3N, was reacted with ethereal diazomethane to afford diazoketone (III). Then, homologation of (III) into b-amino ester (IV) was accomplished by treatment with silver benzoate and Et3N in MeOH. Subsequent hydrolysis of (IV) of the ester function with K2CO3 in aqueous MeOH, followed by Boc deprotection with HCl in dioxan furnished the b-amino acid (VI). After conversion to the trimethylsilyl amine with N-methyl-N-(trimethylsilyl)acetamide, amino acid (VI) was coupled with 2,2'-dithiobisbenzoyl cloride (VIII), prepared from acid (VII) and thionyl chloride, to yield the target bisamide.
【1】 Vara Prasad, J.V.N.; Loo, J.A.; Boyer, F.E.; Stier, M.A.; Gogliotti, R.D.; Turner, W.J.; Harvey, P.J.; Kramer, M.R.; Mack, D.P.; Scholten, J.D.; Gracheck, S.J.; Domagala, J.M.; 2,2'-Dithiobisbenzamides derived from alpha-, beta- and gamma-amino acids possessing anti-HIV activities: Synthesis and structure-activity relationship. Bioorg Med Chem 1998, 6, 10, 1707. |
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) | 20398 | (2S)-2-[(tert-butoxycarbonyl)amino]hexanoic acid | C11H21NO4 | 详情 | 详情 | |
(II) | 20399 | N-(Tert-butoxycarbonyl)-L-norleucine isobutoxycarbonyl anhydride | C16H29NO6 | 详情 | 详情 | |
(III) | 20400 | tert-butyl (1S)-1-[2-(1lambda(5)-diazynyl)acetyl]pentylcarbamate | C12H23N3O3 | 详情 | 详情 | |
(IV) | 20401 | methyl (3S)-3-[(tert-butoxycarbonyl)amino]heptanoate | C13H25NO4 | 详情 | 详情 | |
(V) | 20402 | (3S)-3-[(tert-butoxycarbonyl)amino]heptanoic acid | C12H23NO4 | 详情 | 详情 | |
(VI) | 20403 | (3S)-3-aminoheptanoic acid | C7H15NO2 | 详情 | 详情 | |
(VII) | 20404 | 2-[(2-carboxyphenyl)disulfanyl]benzoic acid; 2,2'-Dithiodibenzoic acid | 119-80-2 | C14H10O4S2 | 详情 | 详情 |
(VIII) | 20405 | 2-[[2-(chlorocarbonyl)phenyl]disulfanyl]benzoyl chloride | C14H8Cl2O2S2 | 详情 | 详情 |