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【结 构 式】

【分子编号】15071

【品名】benzhydryl (6R,7R)-7-[(tert-butoxycarbonyl)amino]-3-([5-(formylamino)-1-[2-(formyloxy)ethyl]-2-iodo-1H-2lambda(5)-pyrazol-2-yl]methyl)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate

【CA登记号】

【 分 子 式 】C33H36IN5O8S

【 分 子 量 】789.64821

【元素组成】C 50.19% H 4.6% I 16.07% N 8.87% O 16.21% S 4.06%

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:(IV)

FK-037 can be obtained by related ways: 1) The formylation of 5-amino-1-(2-hydroxyethyl)pyrazole (I) with formic acid - acetic anhydride gives 5-formamido-1-(2-hydroxyethyl)pyrazole (II), which is condensed with 7beta-(tert-butoxycarbonylamino)-3-(chloromethyl)-3-cephem-4-carboxylic acid diphenylmethyl ester (III) by means of NaI in DMF, yielding 7beta-(tert-butoxycarbonylamino)-3-[3-formamido-2-(2-formyloxyethyl)-1-pyrazoliomethyl]-3-cephem-4-carboxylic acid diphenylmethyl ester iodide (IV). The treatment of (IV), first with trifluoroacetic acid and anisole and then with HCl, affords 7beta-amino-3-[3-amino-2-(2-hydroxyethyl)-1-pyrazoliomethyl]-3-cephem-4-carboxylic acid chloride (V). The condensation of (V) with 2-(2-formamidothiazol-4-yl)-2(Z)-(methoxyimino)acetic acid (VI) by means of POCl3 in ethyl acetate gives 3-[3-amino-2-(2-hydroxyethyl)-1-pyrazoliomethyl]-7beta-[2-(2-formamido-thiazol-4-yl)-2(Z)-(methoxyimino)acetamido]-3-cephem-4-carboxylate (VII), which is deformylated with HCl affording 3-[3-amino-2-(2-hydroxyethyl)-1-pyrazoliomethyl]-7beta-[2-(2-aminothiazol-4-yl)-2(Z)-(methoxyimino)acetamido]-3-cephem-4-carboxylate (VIII). Finally, this compound is treated with H2SO4 to give FK-037. 2) Compound (VIII) can also be obtained by condensation of (V) with 1-[2-(2-aminothiazol-4-yl)-2(Z)-(methoxyimino)acetyl]benzo- triazole-3-oxide (IX) in THF.

1 Sakane, K.; Kawabata, K.; Miyai, K.; Inamoto, Y. (Fujisawa Pharmaceutical Co., Ltd.); New cephem cpd. and process for preparation thereof. AU 8822271; EP 0307804; JP 1989151589; US 4952578 .
2 Sakane, K.; Kawabata, K.; Ohki, H. (Fujisawa Pharmaceutical Co., Ltd.); Process for the preparation of cephalosporin cpd. JP 1992173792 .
3 Ohki, H.; Kawabata, K.; Okuda, S.; Kamimura, T.; Sakane, K.; FK037, a new parenteral cephalosporin with a broad antibacterial spectrum: Synthesis and antibacterial activity. J Antibiot 1993, 46, 2, 359.
4 Prous, J.; Graul, A.; Castaner, J.; FK-037. Drugs Fut 1994, 19, 4, 325.
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) 15068 2-(5-amino-1H-pyrazol-1-yl)-1-ethanol C5H9N3O 详情 详情
(II) 15069 2-[5-(formylamino)-1H-pyrazol-1-yl]ethyl formate C7H9N3O3 详情 详情
(III) 15070 benzhydryl (6R,7R)-7-[(tert-butoxycarbonyl)amino]-3-(chloromethyl)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate C26H27ClN2O5S 详情 详情
(IV) 15071 benzhydryl (6R,7R)-7-[(tert-butoxycarbonyl)amino]-3-([5-(formylamino)-1-[2-(formyloxy)ethyl]-2-iodo-1H-2lambda(5)-pyrazol-2-yl]methyl)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate C33H36IN5O8S 详情 详情
(V) 15072 (6R,7R)-7-amino-3-[[5-amino-2-chloro-1-(2-hydroxyethyl)-1H-2lambda(5)-pyrazol-2-yl]methyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid C33H36IN5O8S 详情 详情
(VI) 15073 2-(2-Formamidothiazole-4-yl)-2-methoxyimino acetic acid; 2-[2-(formylamino)-1,3-thiazol-4-yl]-2-(methoxyimino)acetic acid 83594-38-1 C7H7N3O4S 详情 详情
(VII) 15074 (6R,7R)-3-[[5-amino-1-(2-hydroxyethyl)-1H-pyrazol-2-ium-2-yl]methyl]-7-[[2-[2-(formylamino)-1,3-thiazol-4-yl]-2-(methoxyimino)acetyl]amino]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate C20H22N8O7S2 详情 详情
(VIII) 15075 (6R,7R)-3-[[5-amino-1-(2-hydroxyethyl)-1H-pyrazol-2-ium-2-yl]methyl]-7-[[2-(2-amino-1,3-thiazol-4-yl)-2-(methoxyimino)acetyl]amino]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate C19H22N8O6S2 详情 详情
(IX) 15076 3-[2-(2-amino-1,3-thiazol-4-yl)-2-(methoxyimino)acetyl]-3H-1,2,3-benzotriazol-1-ium-1-olate C12H10N6O3S 详情 详情
Extended Information