tert-butyl (2S)-2-[(1R)-1-([[(1S)-1-benzyl-2-(1H-indol-3-yl)-2-oxoethyl]amino]carbonyl)-3-methylbutyl]-6-heptenoate -Drug Synthesis Database

【结构式】

【分子编号】21656

【品名】tert-butyl (2S)-2-[(1R)-1-([[(1S)-1-benzyl-2-(1H-indol-3-yl)-2-oxoethyl]amino]carbonyl)-3-methylbutyl]-6-heptenoate

【CA登记号】

【分子式】C₃₄H₄₄N₂O₄

【分子量】544.73444

【元素组成】C 74.97% H 8.14% N 5.14% O 11.75%

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)

Friedel Crafts acylation of indole (II) with phenylalanine N-carboxyanhydride (I) in the presence of AlCl3 gave aminoketone (III). Subsequent condensation of (III) with the succinate building block (IV) in DMF afforded succinamide (V). Further deprotection of the tert-butyl ester of (V) by treatment with trifluoroacetic acid provided carboxylic acid (VI), which was coupled with O-tert-butyldimethylsilyl hydroxylamine (VII) in the presence of EDC and HOBt to yield, after desilylation, the target hydroxamic acid.

参考文献中间体

合成目标

【1】 Sheppard, G.S.; Florjancic, A.S.; Giesler, J.R.; Xu, L.; Guo, Y.; Davidsen, S.K.; Marcotte, P.A.; Elmore, I.; Albert, D.H.; Terrance, J.M.; Bouska, J.J.; Goodfellow, C.L.; Morgan, D.W.; Summers, J.B.; Aryl ketones as novel replacements for the C-terminal amide bond of succinyl hydroxamate MMP inhibitors. Bioorg Med Chem Lett 1998, 8, 22, 3251.

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)	21645	(4S)-4-benzyl-1,3-oxazolidine-2,5-dione	14825-82-2	C₁₀H₉NO₃	详情	详情
(II)	15292	Indole; 1H-indole	120-72-9	C₈H₇N	详情	详情
(III)	21647	(2S)-2-amino-1-(1H-indol-3-yl)-3-phenyl-1-propanone		C₁₇H₁₆N₂O	详情	详情
(IV)	21641	1-(tert-butyl) 4-(2,3,4,5,6-pentafluorophenyl) (2S,3R)-2-allyl-3-isobutylbutanedioate		C₂₁H₂₅F₅O₄	详情	详情
(IV)	21655	4-(tert-butyl) 1-(2,3,4,5,6-pentafluorophenyl) (2R,3S)-2-isobutyl-3-(4-pentenyl)butanedioate		C₂₃H₂₉F₅O₄	详情	详情
(V)	21649	tert-butyl (2S)-2-[(1R)-1-([[(1S)-1-benzyl-2-(1H-indol-3-yl)-2-oxoethyl]amino]carbonyl)-3-methylbutyl]-4-pentenoate		C₃₂H₄₀N₂O₄	详情	详情
(V)	21656	tert-butyl (2S)-2-[(1R)-1-([[(1S)-1-benzyl-2-(1H-indol-3-yl)-2-oxoethyl]amino]carbonyl)-3-methylbutyl]-6-heptenoate		C₃₄H₄₄N₂O₄	详情	详情
(VI)	21650	(2S)-2-[(1R)-1-([[(1S)-1-benzyl-2-(1H-indol-3-yl)-2-oxoethyl]amino]carbonyl)-3-methylbutyl]-4-pentenoic acid		C₂₈H₃₂N₂O₄	详情	详情
(VI)	21657	(2S)-2-[(1R)-1-([[(1S)-1-benzyl-2-(1H-indol-3-yl)-2-oxoethyl]amino]carbonyl)-3-methylbutyl]-6-heptenoic acid		C₃₀H₃₆N₂O₄	详情	详情
(VII)	21644	(Aminooxy)(tert-butyl)dimethylsilane; O-[tert-Butyl(dimethyl)silyl]hydroxylamine	41879-39-4	C₆H₁₇NOSi	详情	详情

Extended Information