tert-butyl (8S,11S)-8-isopropyl-7,10-dioxo-2-oxa-6,9-diazabicyclo[11.2.2]heptadeca-1(15),13,16-trien-11-ylcarbamate -Drug Synthesis Database

【结构式】

【分子编号】47892

【品名】tert-butyl (8S,11S)-8-isopropyl-7,10-dioxo-2-oxa-6,9-diazabicyclo[11.2.2]heptadeca-1(15),13,16-trien-11-ylcarbamate

【CA登记号】

【分子式】C₂₂H₃₃N₃O₅

【分子量】419.52124

【元素组成】C 62.99% H 7.93% N 10.02% O 19.07%

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：(VII)

Coupling on N-Boc-L-valine (I) with 3-bromopropylamine (II) by means of HBTU afforded amide (III). After Boc group cleavage in (III) using trifluoroacetic acid, the resultant amine (IV) was coupled with N-Boc-L-tyrosine (V) to yield the dipeptide amide (VI). Intramolecular cyclization of (VI) to produce the macrocycle (VII) was achieved by treatment with cesium carbonate in the presence of tetrabutylammonium iodide. Subsequent acid cleavage of the Boc protecting group of (VII) furnished the intermediate amine (VIII).

参考文献中间体

合成目标

【1】 Mak, C.C.; Le, V.-D.; Wong, C.-H.; Elder, J.H.; Lin, Y.-C.; Design, synthesis, and biological evaluation of HIV/FIV protease inhibitors incorporating a conformationally constrained macrocycle with a small P3' residue. Bioorg Med Chem Lett 2001, 11, 2, 219.

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)	19733	(2S)-2-[(tert-butoxycarbonyl)amino]-3-methylbutyric acid		C₁₀H₁₉NO₄	详情	详情
(II)	25449	3-bromo-1-propanamine; 3-bromopropylamine	18370-81-5	C₃H₈BrN	详情	详情
(III)	47889	tert-butyl (1S)-1-[[(3-bromopropyl)amino]carbonyl]-2-methylpropylcarbamate		C₁₃H₂₅BrN₂O₃	详情	详情
(IV)	47890	(2S)-2-amino-N-(3-bromopropyl)-3-methylbutanamide		C₈H₁₇BrN₂O	详情	详情
(V)	25395	(2S)-2-[(tert-butoxycarbonyl)amino]-3-(4-hydroxyphenyl)propionic acid	3978-80-1	C₁₄H₁₉NO₅	详情	详情
(VI)	47891	tert-butyl (1S)-2-[((1S)-1-[[(3-bromopropyl)amino]carbonyl]-2-methylpropyl)amino]-1-(4-hydroxybenzyl)-2-oxoethylcarbamate		C₂₂H₃₄BrN₃O₅	详情	详情
(VII)	47892	tert-butyl (8S,11S)-8-isopropyl-7,10-dioxo-2-oxa-6,9-diazabicyclo[11.2.2]heptadeca-1(15),13,16-trien-11-ylcarbamate		C₂₂H₃₃N₃O₅	详情	详情
(VIII)	47893	(8S,11S)-11-amino-8-isopropyl-2-oxa-6,9-diazabicyclo[11.2.2]heptadeca-1(15),13,16-triene-7,10-dione		C₁₇H₂₅N₃O₃	详情	详情

Extended Information