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【结 构 式】

【分子编号】11155

【品名】4-methoxybenzyl (7R)-7-amino-3-[(Z)-2-(4-methyl-1,3-thiazol-5-yl)ethenyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate

【CA登记号】

【 分 子 式 】C21H21N3O4S2

【 分 子 量 】443.54756

【元素组成】C 56.87% H 4.77% N 9.47% O 14.43% S 14.46%

与该中间体有关的原料药合成路线共 2 条

合成路线1

该中间体在本合成路线中的序号:(IV)

1 Sakagsmi K, Atsumi K, Yamamoto Y,et aL 1991. Synthesis and activity of pivaloyloxymethyl一[( Z-(2-anunothiazol-4-yD-2-methoxyiminoaceuunido]一3(Z)-(4-methylthiazol-5-yl) vinyl-3-cepllern-4-carbox)rlate (ME1207) and its related compound. Chem Pharm Bull, 39 (9): 2433^-2436
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) 11151 4-methoxybenzyl (7R)-3-(chloromethyl)-8-oxo-7-[(2-phenylacetyl)amino]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate 104146-10-3 C24H23ClN2O5S 详情 详情
(II) 11153 4-Methyl-1,3-thiazole-5-carbaldehyde 82294-70-0 C5H5NOS 详情 详情
(III) 11154 4-methoxybenzyl (7R)-3-[(Z)-2-(4-methyl-1,3-thiazol-5-yl)ethenyl]-8-oxo-7-[(2-phenylacetyl)amino]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate C29H27N3O5S2 详情 详情
(IV) 11155 4-methoxybenzyl (7R)-7-amino-3-[(Z)-2-(4-methyl-1,3-thiazol-5-yl)ethenyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate C21H21N3O4S2 详情 详情
(V) 66179 (Z)-3-methoxy-2-(2-(tritylamino)thiazol-4-yl)acrylic acid   C26H22N2O3S 详情 详情

合成路线2

该中间体在本合成路线中的序号:(V)

The reaction of 3-(chloromethyl)-7-(phenylacetamido)-3-cephem-4-carboxylic acid 4-methoxybenzyl ester (I) with triphenylphosphine and NaI in acetone gives the corresponding phosphonium salt (II), which is condensed with 4-methylthiazole-5-carboxaldehyde (III) by means of NaHCO3 in dichloromethane affording 3-[2(Z)-(4-methylthiazol-5-yl)vinyl]-7-(phenylacetamido)-3-cephem-4-carboxylic acid 4-methoxybenzyl ester (IV). The cleavage of the amido group of (IV) with PCl5 and pyridine yields the 7-amino compound (V), which is condensed with 2-(methoxyimino)-2-[2-(tritylamino)thiazol-4-yl]acetic acid (VI) by means of POCl3 in dichloromethane giving 3-[2(Z)-(4-methylthiazol-5-yl)vinyl]-7-[2(Z)-methoxyimino)-2-(2-tritylamino)thiazol-4-yl)acetamido]-3-cephem-4-carboxylic acid 4-methoxybenzyl ester (VII). The deprotection of (VII) with trifluoroacetic acid and anisole yields the free amino acid (VIII), which is finally esterified with iodomethyl pivalate (IX) in DMF.

1 Yamamoto, Y.; Yoshida, T.; Tamura, A.; Atsumi, K.; Fukatsu, S.; Sakagami, K.; Nishihata, K.; Synthesis and oral activity of pivaloyloxymethyl 7-[(Z)-2-(2-aminothiazol-4-yl)-2-methoxyiminoacetamido]-3(Z)--(4-methylthiazol-5-yl)vinyl-3-cephem-4-carboxylate (ME1207) and its related compound. Chem Pharm Bull 1992, 39, 9, 2433.
2 Atsumi, K.; Sakagami, K.; Yamamoto, Y.; Yoshida, T.; Nishihata, K.; Kondo, S.; Fukatsu, S. (Meiji Seika Kaisha, Ltd.); New cephalosporin cpds. and the production thereof. EP 0175610; ES 8704955; JP 1986178991; JP 1987019593 .
3 Castaner, J.; Prous, J.; Cefditoren Pivoxil. Drugs Fut 1992, 17, 8, 665.
4 Sakagami, K.; Tamura, A.; Yoshida, T.; Nishihata, K.; Fukatsu, S.; Atsumi, K.; Synthesis and oral activity of ME1207, a new orally active cephalosporin. J Antibiot 1990, 43, 8, 1047.
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) 11151 4-methoxybenzyl (7R)-3-(chloromethyl)-8-oxo-7-[(2-phenylacetyl)amino]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate 104146-10-3 C24H23ClN2O5S 详情 详情
(II) 11152 4-methoxybenzyl (7R)-8-oxo-7-[(2-phenylacetyl)amino]-3-[(triphenylphosphoranyl)methyl]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate C42H39N2O5PS 详情 详情
(III) 11153 4-Methyl-1,3-thiazole-5-carbaldehyde 82294-70-0 C5H5NOS 详情 详情
(IV) 11154 4-methoxybenzyl (7R)-3-[(Z)-2-(4-methyl-1,3-thiazol-5-yl)ethenyl]-8-oxo-7-[(2-phenylacetyl)amino]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate C29H27N3O5S2 详情 详情
(V) 11155 4-methoxybenzyl (7R)-7-amino-3-[(Z)-2-(4-methyl-1,3-thiazol-5-yl)ethenyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate C21H21N3O4S2 详情 详情
(VI) 11156 2-(Methoxyimino)-2-[2-(tritylamino)-1,3-thiazol-4-yl]acetamide C25H22N4O2S 详情 详情
(VII) 11157 4-methoxybenzyl (7R)-7-[[2-(2-amino-1,3-thiazol-4-yl)-2-(methoxyimino)acetyl]amino]-3-[(Z)-2-(4-methyl-1,3-thiazol-5-yl)ethenyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate C27H26N6O6S3 详情 详情
(VIII) 11158 (7R)-7-[[2-(2-Amino-1,3-thiazol-4-yl)-2-(methoxyimino)acetyl]amino]-3-[(Z)-2-(4-methyl-1,3-thiazol-5-yl)ethenyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid C19H18N6O5S3 详情 详情
(IX) 11159 iodomethyl pivalate C6H11IO2 详情 详情
Extended Information