5-methylhexanoic acid -Drug Synthesis Database

【结构式】

【分子编号】27649

【品名】5-methylhexanoic acid

【CA登记号】628-46-6

【分子式】C₇H₁₄O₂

【分子量】130.18696

【元素组成】C 64.58% H 10.84% O 24.58%

与该中间体有关的原料药合成路线共 2 条

合成路线1 合成路线2

合成路线1

该中间体在本合成路线中的序号：(XXI)

Successive deprotection/coupling cycles of peptide resin (XV) with Fmoc-L-Val-OH (XVI), Fmoc-L-Thr(tBu)-OH (XVIII), Fmoc-D-Val-OH (I) and 5-methylhexanoic acid (XXI) give peptide resins (XVII), (XIX), (XX) and (XXII), respectively.

参考文献中间体

合成目标

【1】 Royo, M.; Manzanares, I.; Lopez, A.; Jimenez, J.C.; Albericio, F.; Giralt, E.; Rodrigues, I. (PharmaMar, SA); Kahalalide cpds.. WO 0158934 .

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)	43354	(2R)-2-[[(9H-fluoren-9-ylmethoxy)carbonyl]amino]-3-methylbutyric acid		C₂₀H₂₁NO₄	详情	详情
(XV)	49385	(2-chlorophenyl)(diphenyl)methyl (9S,12R,15R,18R,21R)-15-[(1R)-1-[((2S)-2-[[(allyloxy)carbonyl]amino]-3-methylbutanoyl)oxy]ethyl]-9-[([1-[(2R)-2-amino-3-methylbutanoyl]-2-pyrrolidinyl]carbonyl)amino]-21-isopropyl-2,2-dimethyl-12,18-bis[(1S)-1-methylpropyl]-4,10,13,16,19-pentaoxo-3-oxa-5,11,14,17,20-pentaazadocosan-22-oate		C₆₉H₁₀₀ClN₉O₁₄	详情	详情
(XVI)	19932	(2S)-2-[[(9H-fluoren-9-ylmethoxy)carbonyl]amino]-3-methylbutyric acid		C₂₀H₂₁NO₄	详情	详情
(XVII)	49386	(2-chlorophenyl)(diphenyl)methyl (9S,12R,15R,18R,21R)-15-[(1R)-1-[((2S)-2-[[(allyloxy)carbonyl]amino]-3-methylbutanoyl)oxy]ethyl]-9-([[1-((2R)-2-[[(2S)-2-amino-3-methylbutanoyl]amino]-3-methylbutanoyl)-2-pyrrolidinyl]carbonyl]amino)-21-isopropyl-2,2-dimethyl-12,18-bis[(1S)-1-methylpropyl]-4,10,13,16,19-pentaoxo-3-oxa-5,11,14,17,20-pentaazadocosan-22-oate		C₇₄H₁₀₉ClN₁₀O₁₅	详情	详情
(XVIII)	18847	(2S,3R)-3-(tert-butoxy)-2-[[(9H-fluoren-9-ylmethoxy)carbonyl]amino]butyric acid		C₂₃H₂₇NO₅	详情	详情
(XIX)	49387	(2-chlorophenyl)(diphenyl)methyl (9S,12R,15R,18R,21R)-15-[(1R)-1-[((2S)-2-[[(allyloxy)carbonyl]amino]-3-methylbutanoyl)oxy]ethyl]-9-[[(1-[(2R)-2-[((2S)-2-[[(2S)-2-amino-3-(tert-butoxy)butanoyl]amino]-3-methylbutanoyl)amino]-3-methylbutanoyl]-2-pyrrolidinyl)carbonyl]amino]-21-isopropyl-2,2-dimethyl-12,18-bis[(1S)-1-methylpropyl]-4,10,13,16,19-pentaoxo-3-oxa-5,11,14,17,20-pentaazadocosan-22-oate		C₈₂H₁₂₄ClN₁₁O₁₇	详情	详情
(XX)	49388			C₈₇H₁₃₃ClN₁₂O₁₈	详情	详情
(XXI)	27649	5-methylhexanoic acid	628-46-6	C₇H₁₄O₂	详情	详情
(XXII)	49389	(2-chlorophenyl)(diphenyl)methyl (9S,12R,15R,18R,21R)-15-[(1R)-1-[((2S)-2-[[(allyloxy)carbonyl]amino]-3-methylbutanoyl)oxy]ethyl]-9-[[(1-[(2R,5S,8S,11R)-8-[1-(tert-butoxy)ethyl]-2,5,11-triisopropyl-17-methyl-4,7,10,13-tetraoxo-3,6,9,12-tetraazaoctadec-1-anoyl]-2-pyrrolidinyl)carbonyl]amino]-21-isopropyl-2,2-dimethyl-12,18-bis[(1S)-1-methylpropyl]-4,10,13,16,19-pentaoxo-3-oxa-5,11,14,17,20-pentaazadocosan-22-oate		C₉₄H₁₄₅ClN₁₂O₁₉	详情	详情

合成路线2

该中间体在本合成路线中的序号：(II)

The acylation of 6-amino-5-(benzylamino)-2-methylpyrimidine-2,4(1H,3H)-dione (I) with 5-methylhexanoic acid (II) by means of EDCI and DMAP gives the amide (III), which is cyclized by means of hot POCl3 affording the chloropurin-6-one (IV). The condensation of (IV) with the chiral aminoalcohol (V) by means of DIEA and NMP yields intermediate (VI), which is cyclized by means of SOCl2 in dichloromethane providing the imidazo-purine (VII). Finally, this compound is debenzylated with ammonium formate and Pd(OH)2.

参考文献中间体

合成目标

【1】 Ho, G.D.; Silverman, L.; Bercovivi, A.; Puchalski, C.; Tulshian, D.; Xia, Y.; Czarniecki, M.; Green, M.; Cleven, R.; Zhang, H.; Fawzi, A.; Synthesis and evaluation of potent and selective c-GMP phosphodiesterase inhibitors. Bioorg Med Chem Lett 1999, 9, 1, 7.

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)	27648	6-amino-5-(benzylamino)-3-methyl-2,4(1H,3H)-pyrimidinedione		C₁₂H₁₄N₄O₂	详情	详情
(II)	27649	5-methylhexanoic acid	628-46-6	C₇H₁₄O₂	详情	详情
(III)	27650	N-(6-amino-3-methyl-2,4-dioxo-1,2,3,4-tetrahydro-5-pyrimidinyl)-N-benzyl-5-methylhexanamide		C₁₉H₂₆N₄O₃	详情	详情
(IV)	27651	7-benzyl-2-chloro-1-methyl-8-(4-methylpentyl)-1,7-dihydro-6H-purin-6-one		C₁₉H₂₃ClN₄O	详情	详情
(V)	27652	(2R)-2-amino-3-methyl-1-butanol; (R-(-))-Valinol; D-Valinol	4276-09-9	C₅H₁₃NO	详情	详情
(VI)	27653	7-benzyl-2-[[(1R)-1-(hydroxymethyl)-2-methylpropyl]amino]-1-methyl-8-(4-methylpentyl)-1,7-dihydro-6H-purin-6-one		C₂₄H₃₅N₅O₂	详情	详情
(VII)	27654	(7R)-3-benzyl-7-isopropyl-5-methyl-2-(4-methylpentyl)-7,8-dihydro-3H-imidazo[2,1-b]purin-4(5H)-one		C₂₄H₃₃N₅O	详情	详情

Extended Information