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【结 构 式】

【分子编号】19844

【品名】benzhydryl (6S,7S)-7-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)-3-methyl-8-oxo-4-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate

【CA登记号】

【 分 子 式 】C29H22N2O5S

【 分 子 量 】510.57016

【元素组成】C 68.22% H 4.34% N 5.49% O 15.67% S 6.28%

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:(V)

The D-threonine (I) is converted into the azetidinone (II), and into the enol (III) according to (Tsubouchi, H., et al. Tetrahedron Assimetry, 1944, 5: 441). The tosylation of (III) with tosyl chloride and N-methylpyrrolidine yielded the tosylated enol (IV), which was cyclized with H2S and triethylamine to the isocephem derivative (V). The chlorination of (V) with N-bromosuccinimide (NBS) and AIBN affords the bromomethyl derivative (VI), which is treated with 2-(4-methyl-2-sulfanylthiazol-5-yl)acetic acid (VII) and triethylamine or NaHCO3 and then esterified with diphenyldiazomethane to give the expected condensation product (VIII). The reaction of (VIII) with methylhydrazine cleaves the phthalimide group affording (IX), which is then amidated wih the acetic acid derivative (X) by means of dicyclohexylcarbodiimide (DCC) givig the fully protected final product (XI). Finally, this compound is treated with trifluoroacetic acid to eliminate the diphenyl nad triphenyl protecting groups.

1 Tsuji, K.; et al.; Synthesis and structure-activity relationships of cephalosporins, 2-isocephems, and 2-oxaisocephems with C-3' or C-7 catechol or related aromatics. Bioorg Med Chem 1996, 4, 12, 2135.
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) 19840 (2R,3S)-3-hydroxy-2-methylbutyric acid C5H10O3 详情 详情
(II) 19841 benzhydryl (2R,3S)-2-[(3S,4R)-3-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)-2-oxo-4-[(E)-2-phenylethenyl]azetidinyl]-3-hydroxybutanoate C36H30N2O6 详情 详情
(III) 19842 benzhydryl (Z)-2-((2R,3S)-3-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)-2-[[methyl(dimethylene)-lambda(6)-sulfanyl]oxy]-4-oxoazetidinyl)-3-hydroxy-2-butenoate C31H28N2O7S 详情 详情
(IV) 19843 benzhydryl (Z)-2-((2R,3S)-3-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)-2-[[methyl(dimethylene)-lambda(6)-sulfanyl]oxy]-4-oxoazetidinyl)-3-[[(4-methylphenyl)sulfonyl]oxy]-2-butenoate C38H34N2O9S2 详情 详情
(V) 19844 benzhydryl (6S,7S)-7-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)-3-methyl-8-oxo-4-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate C29H22N2O5S 详情 详情
(VI) 19845 benzhydryl (6S,7S)-3-(bromomethyl)-7-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)-8-oxo-4-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate C29H21BrN2O5S 详情 详情
(VII) 19846 2-(4-methyl-2-sulfanyl-1,3-thiazol-5-yl)acetic acid 34272-64-5 C6H7NO2S2 详情 详情
(VIII) 19847 benzhydryl (6S,7S)-3-[([5-[2-(benzhydryloxy)-2-oxoethyl]-4-methyl-1,3-thiazol-2-yl]sulfanyl)methyl]-7-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)-8-oxo-4-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate C48H37N3O7S3 详情 详情
(IX) 19848 benzhydryl (6S,7S)-7-amino-3-[([5-[2-(benzhydryloxy)-2-oxoethyl]-4-methyl-1,3-thiazol-2-yl]sulfanyl)methyl]-8-oxo-4-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate C40H35N3O5S3 详情 详情
(X) 19849 2-([[1,5-bis(benzhydryloxy)-4-oxo-1,4-dihydro-2-pyridinyl]methoxy]imino)-2-[2-(tritylamino)-1,3-thiazol-4-yl]acetic acid C56H44N4O6S 详情 详情
(XI) 19850 benzhydryl (6S,7S)-3-[([5-[2-(benzhydryloxy)-2-oxoethyl]-4-methyl-1,3-thiazol-2-yl]sulfanyl)methyl]-7-([2-([[1,5-bis(benzhydryloxy)-4-oxo-1,4-dihydro-2-pyridinyl]methoxy]imino)-2-[2-(tritylamino)-1,3-thiazol-4-yl]acetyl]amino)-8-oxo-4-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate C96H77N7O10S4 详情 详情
Extended Information