2-[(tert-butoxycarbonyl)amino]benzoic acid -Drug Synthesis Database

【结构式】

【分子编号】45324

【品名】2-[(tert-butoxycarbonyl)amino]benzoic acid

【CA登记号】

【分子式】C₁₂H₁₅NO₄

【分子量】237.25544

【元素组成】C 60.75% H 6.37% N 5.9% O 26.97%

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：(III)

The protection of aniline (I) with di-tert-butyl dicarbonate in THF gives the carbamate (II), which is treated with BuLi and 14C labeled CO2 in THF yielding 2-(tert-butoxycarbonylamino)benzoic acid (III). The deprotection of (III) with TFA in dichloromethane affords labeled 2-aminobenzoic acid (IV), which is diazotized with NaNO2 /HCl and treated with Na2S, S and NaOH to give the disulfide (V). The reaction of (V) with refluxing SOCl2 yields the acid dichloride (VI), which is condensed with L-isoleucine tert-butyl ester (VII), by means of N-methylmorpholine (NMM) in dichloromethane to afford the final intermediate (VIII). Finally, this compound is deprotected with TFA in dichloromethane to give the labeled target compound.

参考文献中间体

合成目标

【1】 Fiore, P.J.; et al.; Development and pilot-scale demonstration of a process for inhibitors of the HIV nucleocapsid protein, NCp7. Org Process Res Dev 1998, 2, 3, 151.

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)	12294	Aniline; Phenylamine	62-53-3	C₆H₇N	详情	详情
(II)	32735	tert-butyl phenylcarbamate	3422-01-3	C₁₁H₁₅NO₂	详情	详情
(III)	32736	2-[(tert-butoxycarbonyl)amino]benzoic acid	68790-38-5	C₁₂H₁₅NO₄	详情	详情
(III)	45324	2-[(tert-butoxycarbonyl)amino]benzoic acid		C₁₂H₁₅NO₄	详情	详情
(IV)	11661	2-Aminobenzoic acid;Anthranilic acid; o-Aminobenzoic acid	118-92-3	C₇H₇NO₂	详情	详情
(IV)	45325	2-aminobenzoic acid		C₇H₇NO₂	详情	详情
(V)	20404	2-[(2-carboxyphenyl)disulfanyl]benzoic acid; 2,2'-Dithiodibenzoic acid	119-80-2	C₁₄H₁₀O₄S₂	详情	详情
(V)	45326	2-[(2-carboxyphenyl)disulfanyl]benzoic acid		C₁₄H₁₀O₄S₂	详情	详情
(VI)	20405	2-[[2-(chlorocarbonyl)phenyl]disulfanyl]benzoyl chloride		C₁₄H₈Cl₂O₂S₂	详情	详情
(VI)	45327	2-[[2-(chlorocarbonyl)phenyl]disulfanyl]benzoyl chloride		C₁₄H₈Cl₂O₂S₂	详情	详情
(VII)	32737	tert-butyl (2S,3S)-2-amino-3-methylpentanoate		C₁₀H₂₁NO₂	详情	详情
(VIII)	32738	tert-butyl (2S,3S)-2-[(2-[[2-([[(1S,2S)-1-(tert-butoxycarbonyl)-2-methylbutyl]amino]carbonyl)phenyl]disulfanyl]benzoyl)amino]-3-methylpentanoate		C₃₄H₄₈N₂O₆S₂	详情	详情
(VIII)	45328	tert-butyl (2S,3S)-2-[(2-[[2-([[(1S,2S)-1-(tert-butoxycarbonyl)-2-methylbutyl]amino]carbonyl)phenyl]disulfanyl]benzoyl)amino]-3-methylpentanoate		C₃₄H₄₈N₂O₆S₂	详情	详情

合成路线2

该中间体在本合成路线中的序号：(III)

The protection of aniline (I) with di-tert-butyl dicarbonate in THF gives the carbamate (II), which is treated with BuLi and 14C labeled CO2 in THF yielding 2-(tert-butoxycarbonylamino)benzoic acid (III). The deprotection of (III) with TFA in dichloromethane affords labeled 2-aminobenzoic acid (IV), which is diazotized with NaNO2 /HCl and treated with Na2S, S and NaOH to give the disulfide (V). The reaction of (V) with refluxing SOCl2 yields the acid dichloride (VI), which is condensed with L-isoleucine tert-butyl ester (VII), by means of N-methylmorpholine (NMM) in dichloromethane to afford the intermediate (VIII). The deprotectionof (VIII) with TFA in dichloromethane to give the labeled dimeric isoleucine derivative (IX), which is finally cyclized to the target benazoisothiazolone by oxidative cyclization with Br2 in dichloromethane.

参考文献中间体

合成目标

【1】 Fiore, P.J.; et al.; Development and pilot-scale demonstration of a process for inhibitors of the HIV nucleocapsid protein, NCp7. Org Process Res Dev 1998, 2, 3, 151.

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)	12294	Aniline; Phenylamine	62-53-3	C₆H₇N	详情	详情
(II)	32735	tert-butyl phenylcarbamate	3422-01-3	C₁₁H₁₅NO₂	详情	详情
(III)	32736	2-[(tert-butoxycarbonyl)amino]benzoic acid	68790-38-5	C₁₂H₁₅NO₄	详情	详情
(III)	45324	2-[(tert-butoxycarbonyl)amino]benzoic acid		C₁₂H₁₅NO₄	详情	详情
(IV)	11661	2-Aminobenzoic acid;Anthranilic acid; o-Aminobenzoic acid	118-92-3	C₇H₇NO₂	详情	详情
(IV)	45325	2-aminobenzoic acid		C₇H₇NO₂	详情	详情
(V)	20404	2-[(2-carboxyphenyl)disulfanyl]benzoic acid; 2,2'-Dithiodibenzoic acid	119-80-2	C₁₄H₁₀O₄S₂	详情	详情
(V)	45326	2-[(2-carboxyphenyl)disulfanyl]benzoic acid		C₁₄H₁₀O₄S₂	详情	详情
(VI)	20405	2-[[2-(chlorocarbonyl)phenyl]disulfanyl]benzoyl chloride		C₁₄H₈Cl₂O₂S₂	详情	详情
(VI)	45327	2-[[2-(chlorocarbonyl)phenyl]disulfanyl]benzoyl chloride		C₁₄H₈Cl₂O₂S₂	详情	详情
(VII)	32737	tert-butyl (2S,3S)-2-amino-3-methylpentanoate		C₁₀H₂₁NO₂	详情	详情
(VIII)	32738	tert-butyl (2S,3S)-2-[(2-[[2-([[(1S,2S)-1-(tert-butoxycarbonyl)-2-methylbutyl]amino]carbonyl)phenyl]disulfanyl]benzoyl)amino]-3-methylpentanoate		C₃₄H₄₈N₂O₆S₂	详情	详情
(VIII)	45328	tert-butyl (2S,3S)-2-[(2-[[2-([[(1S,2S)-1-(tert-butoxycarbonyl)-2-methylbutyl]amino]carbonyl)phenyl]disulfanyl]benzoyl)amino]-3-methylpentanoate		C₃₄H₄₈N₂O₆S₂	详情	详情
(IX)	32740	(2S,3S)-2-[(2-[[2-([[(1S,2S)-1-carboxy-2-methylbutyl]amino]carbonyl)phenyl]disulfanyl]benzoyl)amino]-3-methylpentanoic acid		C₂₆H₃₂N₂O₆S₂	详情	详情
(IX)	45329	(2S,3S)-2-[(2-[[2-([[(1S,2S)-1-carboxy-2-methylbutyl]amino]carbonyl)phenyl]disulfanyl]benzoyl)amino]-3-methylpentanoic acid		C₂₆H₃₂N₂O₆S₂	详情	详情

Extended Information