(7S)-7-[(tert-butoxycarbonyl)amino]-10-[(imino[[(4-methylphenyl)sulfonyl]amino]methyl)amino]-6-oxodecanoic acid -Drug Synthesis Database

【结构式】

【分子编号】37333

【品名】(7S)-7-[(tert-butoxycarbonyl)amino]-10-[(imino[[(4-methylphenyl)sulfonyl]amino]methyl)amino]-6-oxodecanoic acid

【CA登记号】

【分子式】C₂₃H₃₆N₄O₇S

【分子量】512.6276

【元素组成】C 53.89% H 7.08% N 10.93% O 21.85% S 6.26%

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：(VI)

Nalpha-Boc-Ngamma-tosyl-L-arginine (I) was converted to the N,O-dimethyl hydroxamate (II) by treatment with dimethylhydroxylamine and BOP. Condensation of (II) with the Grignard reagent (IV), prepared from 6-bromo-1-hexene (III), produced ketone (V). Then, oxidative cleavage of the terminal alkene of (V) by means of NaIO4 and RuCl3 yielded carboxylic acid (VI).

参考文献中间体

合成目标

【1】 DiMaio, J. (National Research Council of Canada); Thrombin inhibitors based on the amino acid sequence of hirudin. JP 1999502203; WO 9629347 .

中间体序号	中间体编号	品名	CAS号	分子式	供应商	用于合成
	13361	(Methoxyamino)methane; N,O-Dimethylhydroxylamine	1117-97-1	C₂H₇NO	详情	详情
(I)	19064	(2S)-2-[(tert-butoxycarbonyl)amino]-5-[(imino[[(4-methylphenyl)sulfonyl]amino]methyl)amino]pentanoic acid		C₁₈H₂₈N₄O₆S	详情	详情
(II)	37329	tert-butyl (1S)-4-[(imino[[(4-methylphenyl)sulfonyl]amino]methyl)amino]-1-[[methoxy(methyl)amino]carbonyl]butylcarbamate		C₂₀H₃₃N₅O₆S	详情	详情
(III)	37330	6-bromo-1-hexene	2695-47-8	C₆H₁₁Br	详情	详情
(IV)	37331	bromo(5-hexenyl)magnesium		C₆H₁₁BrMg	详情	详情
(V)	37332	tert-butyl (1S)-1-[3-[(imino[[(4-methylphenyl)sulfonyl]amino]methyl)amino]propyl]-2-oxo-7-octenylcarbamate		C₂₄H₃₈N₄O₅S	详情	详情
(VI)	37333	(7S)-7-[(tert-butoxycarbonyl)amino]-10-[(imino[[(4-methylphenyl)sulfonyl]amino]methyl)amino]-6-oxodecanoic acid		C₂₃H₃₆N₄O₇S	详情	详情

合成路线2

该中间体在本合成路线中的序号：(VI)

Amino acid (VI) was then coupled to the peptide sequence to provide, after trifluoroacetic acid deprotection, resin (XXIII). The terminal D-Phe and L-Pro residues were incorporated as the preformed dipeptide (XXIV). Finally, cleavage of all protecting groups by means of HF in the presence of dimethyl sulfide and anisole furnished the title compound.

参考文献中间体

合成目标

【1】 DiMaio, J. (National Research Council of Canada); Thrombin inhibitors based on the amino acid sequence of hirudin. JP 1999502203; WO 9629347 .

中间体序号	中间体编号	品名	分子式	供应商	用于合成
(VI)	37333	(7S)-7-[(tert-butoxycarbonyl)amino]-10-[(imino[[(4-methylphenyl)sulfonyl]amino]methyl)amino]-6-oxodecanoic acid	C₂₃H₃₆N₄O₇S	详情	详情
(XXII)	37343	(2S)-2-([[(2S)-1-((2S,3S)-2-[[((2S)-1-[(2S,5S,8S)-20-amino-5-benzyl-2-[3-(benzyloxy)-3-oxopropyl]-8-[2-(cyclohexyloxy)-2-oxoethyl]-4,7,10,16-tetraoxo-3,6,9,15-tetraazaicos-1-anoyl]pyrrolidinyl)carbonyl]amino]-3-methylpentanoyl)pyrrolidinyl]carbonyl]amino)-4-methylpentanoic acid	C₆₃H₉₃N₉O₁₄	详情	详情
(XXIII)	37344	(2S)-2-[([(2S)-1-[(2S,3S)-2-([[(2S)-1-((2S,5S,8S,28S)-28-amino-5-benzyl-2-[3-(benzyloxy)-3-oxopropyl]-8-[2-(cyclohexyloxy)-2-oxoethyl]-33-imino-33-[[(4-methylphenyl)sulfonyl]amino]-4,7,10,16,22,27-hexaoxo-3,6,9,15,21,32-hexaazatritriacont-1-anoyl)pyrrolidinyl]carbonyl]amino)-3-methylpentanoyl]pyrrolidinyl]carbonyl)amino]-4-methylpentanoic acid	C₈₁H₁₁₉N₁₃O₁₈S	详情	详情
(XXIV)	28932	(2S)-1-[(2R)-2-[(tert-butoxycarbonyl)amino]-3-phenylpropanoyl]-2-pyrrolidinecarboxylic acid	C₁₉H₂₆N₂O₅	详情	详情

Extended Information