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【结 构 式】

【分子编号】15703

【品名】1-[(isopropoxycarbonyl)oxy]ethyl (6R,7S)-7-[(4-bromo-3-oxobutanoyl)amino]-3-([[(dimethylamino)carbonyl]oxy]methyl)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate

【CA登记号】

【 分 子 式 】C21H28BrN3O10S

【 分 子 量 】594.43754

【元素组成】C 42.43% H 4.75% Br 13.44% N 7.07% O 26.92% S 5.39%

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:(IIIb)

The synthesis of [14C]-labeled E-1101 has been reported: (6R,7R)-7-Amino-3-(N,N-dimethylcarbamoyloxymethyl)-3-cephem-4-carboxyli c acid 1-(isopropoxycarbonyloxy)ethyl ester (I) is a diastereomeric mixture (Ia and Ib) due to the asymmetric carbon in the ester group. These isomers are separated by crystallization in THF and submitted separately to the following reaction sequence: The reaction of (Ia) and (Ib) with diketene (II) and Br2 gives the 4-bromo-3-oxobutyrylamides (IIIa and IIIb), which by oxidation with acetyl chloride and butylnitrite in dichloromethane yield the hydroxyimino derivatives (IVa and IVb). The cyclization of (IVa) and (IVb) with [14C]-labeled thiourea (V) in dimethylacetamide affords the two labeled diastereomeric E-1101 compounds (VIa and VIb), which are finally mixed equimolecularly to obtain the labeled E-1101 racemic at the ester group.

1 Uemura, Y.; Komatsu, Y.; Negi, S.; Tsuruoka, A.; Synthesis of a radiolabelled new oral cephalosporin, E1101. J Label Compd Radiopharm 1996, 38, 1, 1.
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
(Ia) 15699 1-[(isopropoxycarbonyl)oxy]ethyl (6R,7R)-7-amino-3-([[(dimethylamino)carbonyl]oxy]methyl)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate C17H25N3O8S 详情 详情
(Ib) 15700 1-[(isopropoxycarbonyl)oxy]ethyl (6R,7S)-7-amino-3-([[(dimethylamino)carbonyl]oxy]methyl)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate C17H25N3O8S 详情 详情
(IIIa) 15702 1-[(isopropoxycarbonyl)oxy]ethyl (6R,7R)-7-[(4-bromo-3-oxobutanoyl)amino]-3-([[(dimethylamino)carbonyl]oxy]methyl)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate C21H28BrN3O10S 详情 详情
(IIIb) 15703 1-[(isopropoxycarbonyl)oxy]ethyl (6R,7S)-7-[(4-bromo-3-oxobutanoyl)amino]-3-([[(dimethylamino)carbonyl]oxy]methyl)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate C21H28BrN3O10S 详情 详情
(IVa) 15704 1-[(isopropoxycarbonyl)oxy]ethyl (6R,7R)-7-[[4-bromo-2-(hydroxyimino)-3-oxobutanoyl]amino]-3-([[(dimethylamino)carbonyl]oxy]methyl)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate C21H27BrN4O11S 详情 详情
(IVb) 15705 1-[(isopropoxycarbonyl)oxy]ethyl (6R,7S)-7-[[4-bromo-2-(hydroxyimino)-3-oxobutanoyl]amino]-3-([[(dimethylamino)carbonyl]oxy]methyl)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate C21H27BrN4O11S 详情 详情
(VIa) 15707 1-[(isopropoxycarbonyl)oxy]ethyl (6R,7R)-7-[[2-(2-amino-1,3-thiazol-4-yl)-2-(hydroxyimino)acetyl]amino]-3-([[(dimethylamino)carbonyl]oxy]methyl)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate C22H28N6O10S2 详情 详情
(VIb) 15708 1-[(isopropoxycarbonyl)oxy]ethyl (6R,7S)-7-[[2-(2-amino-1,3-thiazol-4-yl)-2-(hydroxyimino)acetyl]amino]-3-([[(dimethylamino)carbonyl]oxy]methyl)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate C22H28N6O10S2 详情 详情
(VIa) 45262 1-[(isopropoxycarbonyl)oxy]ethyl (6R,7R)-7-[[2-(2-amino-1,3-thiazol-4-yl)-2-(hydroxyimino)acetyl]amino]-3-([[(dimethylamino)carbonyl]oxy]methyl)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate C22H28N6O10S2 详情 详情
(VIb) 45263 1-[(isopropoxycarbonyl)oxy]ethyl (6R,7S)-7-[[2-(2-amino-1,3-thiazol-4-yl)-2-(hydroxyimino)acetyl]amino]-3-([[(dimethylamino)carbonyl]oxy]methyl)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate C22H28N6O10S2 详情 详情
(II) 15701 2,4-oxetanedione C3H2O3 详情 详情
(V) 10180 Thiourea 62-56-6 CH4N2S 详情 详情
Extended Information