(2S)-2-[(tert-butoxycarbonyl)(methyl)amino]-5-[[(9H-fluoren-9-ylmethoxy)carbonyl]amino]pentanoic acid -Drug Synthesis Database

【结构式】

【分子编号】38811

【品名】(2S)-2-[(tert-butoxycarbonyl)(methyl)amino]-5-[[(9H-fluoren-9-ylmethoxy)carbonyl]amino]pentanoic acid

【CA登记号】

【分子式】C₂₆H₃₂N₂O₆

【分子量】468.54996

【元素组成】C 66.65% H 6.88% N 5.98% O 20.49%

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：(I)

Condensation of Nalpha-Boc-Ndelta-Fmoc-Nalpha-methyl-L-ornithine (I) with beta-naphthylamine (II) to give the corresponding naphthyl amide (III) was effected by treatment with POCl3 and i-Pr2NEt. The Boc group of (III) was then deprotected by treatment with trifluoroacetic acid, yielding amine (IV). After activation of N-Boc-L-phenylalanine (V) as the mixed anhydride with ethyl chloroformate, coupling with amine (IV) afforded the protected dipeptide (VI). Deprotection of the Fmoc group of (VI) employing piperidine in dimethylacetamide gave (VII). Finally, Boc group cleavage in (VII) by treatment with trifluoroacetic acid furnished the title dipeptide amide.

参考文献中间体

合成目标

【1】 Leger, R.; Zhang, Z.J.; She, M.; Lee, M.; Chamberland, S.; Renau, T.; Lee, V.J. (Microcide Pharmaceuticals, Inc.); Efflux pump inhibitors. WO 9937667 .

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)	38811	(2S)-2-[(tert-butoxycarbonyl)(methyl)amino]-5-[[(9H-fluoren-9-ylmethoxy)carbonyl]amino]pentanoic acid		C₂₆H₃₂N₂O₆	详情	详情
(II)	38812	2-naphthylamine; 2-naphthalenamine	91-59-8	C₁₀H₉N	详情	详情
(III)	38813	9H-fluoren-9-ylmethyl (4S)-4-[(tert-butoxycarbonyl)(methyl)amino]-5-(2-naphthylamino)-5-oxopentylcarbamate		C₃₆H₃₉N₃O₅	详情	详情
(IV)	38814	9H-fluoren-9-ylmethyl (4S)-4-(methylamino)-5-(2-naphthylamino)-5-oxopentylcarbamate		C₃₁H₃₁N₃O₃	详情	详情
(V)	12874	(2R)-2-[(tert-Butoxycarbonyl)amino]-3-phenylpropionic acid; N-alpha-t-BOC-L-Phenylalanine	13734-34-4	C₁₄H₁₉NO₄	详情	详情
(VI)	38815	tert-butyl (1S)-1-benzyl-2-[[(1S)-4-[[(9H-fluoren-9-ylmethoxy)carbonyl]amino]-1-[(2-naphthylamino)carbonyl]butyl](methyl)amino]-2-oxoethylcarbamate		C₄₅H₄₈N₄O₆	详情	详情
(VII)	38816	tert-butyl (1S)-2-[[(1S)-4-amino-1-[(2-naphthylamino)carbonyl]butyl](methyl)amino]-1-benzyl-2-oxoethylcarbamate		C₃₀H₃₈N₄O₄	详情	详情

Extended Information