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【结 构 式】

【分子编号】20402

【品名】(3S)-3-[(tert-butoxycarbonyl)amino]heptanoic acid

【CA登记号】

【 分 子 式 】C12H23NO4

【 分 子 量 】245.31896

【元素组成】C 58.75% H 9.45% N 5.71% O 26.09%

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:(V)

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
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