2-amino-1-ethanesulfonic acid -Drug Synthesis Database

【结构式】

【分子编号】34828

【品名】2-amino-1-ethanesulfonic acid

【CA登记号】107-35-7

【分子式】C₂H₇NO₃S

【分子量】125.14852

【元素组成】C 19.19% H 5.64% N 11.19% O 38.35% S 25.62%

与该中间体有关的原料药合成路线共 3 条

合成路线1 合成路线2 合成路线3

合成路线1

该中间体在本合成路线中的序号：(III)

Ursodeoxycholic acid (I) was activated as the mixed anhydride (II) with ethyl chloroformate and triethylamine, and subsequently coupled with the triethylamine salt of taurine (III) to produce the title conjugated bile acid. Optionally, the mixed anhydride (II) was previously converted to the active phenol ester (V) by treatment with p-hydroxypropiophenone (IV), and subsequently condensed with taurine (III). Alternatively, ursodeoxycholic acid (I) was directly coupled to taurine (III) employing as the coupling reagents 2-isobutyl-N-isobutyloxycarbonyl-1,2-dihydroquinoline (IIDQ), diethylphosphorocyanidate (DEPC), or 2-ethoxy-N-ethoxycarbonyl-1,2-dihydroquinoline (EEDQ) under microwave irradiation.

参考文献中间体

合成目标

【1】 Momose, T.; et al.; An improved synthesis of taurine- and glycine-conjugated bile acids. Lipids 1997, 32, 7, 775.
【2】 Dayal, B.; et al.; Microwave-induced rapid synthesis of bile acid conjugates. Synlett 1997, 8, 861.
【3】 Bonadi, A.; Molinari, E.; Process for the preparation of taurine-conjugated bile acids. EP 0582891 .
【4】 Reiner, A. (SkyePharma AG); Process for preparing ursodeoxycholic acid derivates and their inorganic and organic salts having therapeutic activity. EP 0272462 .

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)	48093	(4R)-4-[(3R,5S,7S,8R,9S,10S,13R,14S,17R)-3,7-dihydroxy-10,13-dimethylhexadecahydro-1H-cyclopenta[a]phenanthren-17-yl]pentanoic acid	128-13-2	C₂₄H₄₀O₄	详情	详情
(II)	59137			C₂₇H₄₄O₆	详情	详情
(III)	34828	2-amino-1-ethanesulfonic acid	107-35-7	C₂H₇NO₃S	详情	详情
(IV)	58982	4'-Hydroxypropiophenone; 4-Hydroxypropiophenone; Ethyl 4-Hydroxyphenyl ktone; p-Hydroxypropiophenone; Paroxypropione	70-70-2	C₉H₁₀O₂	详情	详情
(V)	59138	4-propionylphenyl (4R)-4-[(3R,5S,7S,8R,9S,10S,13R,14S,17R)-3,7-dihydroxy-10,13-dimethylhexadecahydro-1H-cyclopenta[a]phenanthren-17-yl]pentanoate		C₃₃H₄₈O₅	详情	详情

合成路线2

该中间体在本合成路线中的序号：(III)

In a related method, ursodeoxycholic acid (I) was activated as either the mixed anhydrides (VI) or (VII) with pivaloyl chloride or benzoyl chloride, respectively. Subsequent coupling with taurine (III) produced the title conjugated bile acid.

参考文献中间体

合成目标

【1】 Rossetti, V.; Arosio, R. (Sanofi-Synthelabo); Process for the preparation of taurocholic acids. EP 0629634 .

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)	48093	(4R)-4-[(3R,5S,7S,8R,9S,10S,13R,14S,17R)-3,7-dihydroxy-10,13-dimethylhexadecahydro-1H-cyclopenta[a]phenanthren-17-yl]pentanoic acid	128-13-2	C₂₄H₄₀O₄	详情	详情
(III)	34828	2-amino-1-ethanesulfonic acid	107-35-7	C₂H₇NO₃S	详情	详情
(VI)	59139	(4R)-3-[(3R,5S,7S,8R,9S,10S,13R,14S,17R)-3,7-dihydroxy-10,13-dimethylhexadecahydro-1H-cyclopenta[a]phenanthren-17-yl]pentanoic 1,1-dimethylpropanoic anhydride		C₂₉H₄₈O₅	详情	详情
(VII)	59140	1-benzenecarboxylic (4R)-3-[(3R,5S,7S,8R,9S,10S,13R,14S,17R)-3,7-dihydroxy-10,13-dimethylhexadecahydro-1H-cyclopenta[a]phenanthren-17-yl]pentanoic anhydride		C₃₁H₄₄O₅	详情	详情

合成路线3

该中间体在本合成路线中的序号：(II)

The condensation of N-(benzyloxycarbonyl)-L-glutamic acid bis(2,4,6-trichlorophenyl) ester (I) with taurine (II) in the presence of NaOH provided diamide (III). After deprotection of the benzyloxycarbonyl group of (III) by hydrogenolysis over Pd/C, the resulting amine (IV) was coupled with N-palmitoyl-S-(2,3-dilauroyloxypropyl)cysteine (V) using N,N'-dicyclohexylcarbodiimide and N-hydroxynorbornan-2,3-dicarboximide (A) to furnish the title compound.

参考文献中间体

合成目标

【1】 Baschang, G.; Hartmann, A. (Novartis AG); Aminosulphonic acid derivs. and process for their preparation. EP 0548024; JP 1993255239; US 5342977 .

中间体序号	中间体编号	品名	CAS号	分子式	供应商	用于合成
(A)	34832	4-hydroxy-4-azatricyclo[5.2.1.0(2,6)]decane-3,5-dione		C₉H₁₁NO₃	详情	详情
(I)	34827	bis(2,4,6-trichlorophenyl) (2S)-2-[[(benzyloxy)carbonyl]amino]pentanedioate		C₂₅H₁₇Cl₆NO₆	详情	详情
(II)	34828	2-amino-1-ethanesulfonic acid	107-35-7	C₂H₇NO₃S	详情	详情
(III)	34829	disodium 2-([(2S)-2-[[(benzyloxy)carbonyl]amino]-5-oxo-5-[(2-sulfonatoethyl)amino]pentanoyl]amino)-1-ethanesulfonate		C₁₇H₂₃N₃Na₂O₁₀S₂	详情	详情
(IV)	34830	disodium 2-([(2S)-2-amino-5-oxo-5-[(2-sulfonatoethyl)amino]pentanoyl]amino)-1-ethanesulfonate		C₉H₁₇N₃Na₂O₈S₂	详情	详情
(V)	34831	(2R)-3-[[(2R)-2,3-bis(dodecanoyloxy)propyl]sulfanyl]-2-(palmitoylamino)propionic acid		C₄₆H₈₇NO₇S	详情	详情

Extended Information