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【结 构 式】

【分子编号】25066

【品名】[(7-([2-[(cyclopentyloxy)imino]-2-[2-(tritylamino)-1,3-thiazol-4-yl]acetyl]amino)-2-[[(4-methoxybenzyl)oxy]carbonyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-en-3-yl)methyl](triphenyl)phosphonium iodide

【CA登记号】

【 分 子 式 】C63H57IN5O6PS2

【 分 子 量 】1202.185912

【元素组成】C 62.94% H 4.78% I 10.56% N 5.83% O 7.99% P 2.58% S 5.33%

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:(IVc)

The cephalosporin was synthesized following the reaction pathway depicted in Scheme 25490101a: Protected 2-(2-aminothiazol-4-yl)-2-(alkoxy)iminoacetic acid ((Ia-c) was reacted with p-methoxybenzyl 7-amino-3-chloromethyl-cephaslosporonate (II) by a conventional method (POCl3, pyr / CH2Cl2. -5 C) to give the acylated product (IIIa-c). Product (IIIa-c) was then coverted to a phosponium salt (Iva-c) (PPh3, NaI / acetone, r.t.), followed by the reaction (NaHCO3(2N) / CH2Cl2, 0 C - r.t.) with a substituted isoxazole aldehyde (V) to afford the protected final product (Via-c). The aldehyde (V) was prepared by the sequential reduction-oxidation of the 1,3-dipolar cycloaddition product of methyl propiolate and the corresponding aldoxime. Deprotection, sodium salt formation and purification by reverse phase column chromatography (LiChrosorb(R) RP-18, 25% aq. MeOH) followed by frezee drying gave the final product as an amorphous white solid.

1 Choi, K.I.; Discovery of novel 3-isoxazolylvinylcephalosporins. Drugs Fut 1999, 24, 3, 287.
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) 25057 2-[2-(tritylamino)-1,3-thiazol-4-yl]-2-[(trityloxy)imino]acetic acid C43H33N3O3S 详情 详情
(Ib) 25058 2-(methoxyimino)-2-[2-(tritylamino)-1,3-thiazol-4-yl]acetic acid 64485-90-1 C25H21N3O3S 详情 详情
(Ic) 25059 2-[(cyclopentyloxy)imino]-2-[2-(tritylamino)-1,3-thiazol-4-yl]acetic acid C29H27N3O3S 详情 详情
(IIIa) 25061 4-methoxybenzyl 3-(chloromethyl)-8-oxo-7-([2-[2-(tritylamino)-1,3-thiazol-4-yl]-2-[(trityloxy)imino]acetyl]amino)-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate C59H48ClN5O6S2 详情 详情
(IIIb) 25062 4-methoxybenzyl 3-(chloromethyl)-7-([2-(methoxyimino)-2-[2-(tritylamino)-1,3-thiazol-4-yl]acetyl]amino)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate C41H36ClN5O6S2 详情 详情
(IIIc) 25063 4-methoxybenzyl 3-(chloromethyl)-7-([2-[(cyclopentyloxy)imino]-2-[2-(tritylamino)-1,3-thiazol-4-yl]acetyl]amino)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate C45H42ClN5O6S2 详情 详情
(IVa) 25064 [[2-[[(4-methoxybenzyl)oxy]carbonyl]-8-oxo-7-([2-[2-(tritylamino)-1,3-thiazol-4-yl]-2-[(trityloxy)imino]acetyl]amino)-5-thia-1-azabicyclo[4.2.0]oct-2-en-3-yl]methyl](triphenyl)phosphonium iodide C77H63IN5O6PS2 详情 详情
(IVb) 25065 [[2-[[(4-methoxybenzyl)oxy]carbonyl]-7-([2-(methoxyimino)-2-[2-(tritylamino)-1,3-thiazol-4-yl]acetyl]amino)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-en-3-yl]methyl](triphenyl)phosphonium iodide C59H51IN5O6PS2 详情 详情
(IVc) 25066 [(7-([2-[(cyclopentyloxy)imino]-2-[2-(tritylamino)-1,3-thiazol-4-yl]acetyl]amino)-2-[[(4-methoxybenzyl)oxy]carbonyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-en-3-yl)methyl](triphenyl)phosphonium iodide C63H57IN5O6PS2 详情 详情
(VIa) 25068 4-methoxybenzyl 3-[(E)-2-(3-chloro-5-isoxazolyl)ethenyl]-8-oxo-7-([2-[2-(tritylamino)-1,3-thiazol-4-yl]-2-[(trityloxy)imino]acetyl]amino)-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate C63H49ClN6O7S2 详情 详情
(VIb) 25069 4-methoxybenzyl 3-[(E)-2-(3-chloro-5-isoxazolyl)ethenyl]-7-([2-(methoxyimino)-2-[2-(tritylamino)-1,3-thiazol-4-yl]acetyl]amino)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate C45H37ClN6O7S2 详情 详情
(VIc) 25070 4-methoxybenzyl 3-[(E)-2-(3-chloro-5-isoxazolyl)ethenyl]-7-([2-[(cyclopentyloxy)imino]-2-[2-(tritylamino)-1,3-thiazol-4-yl]acetyl]amino)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate C49H43ClN6O7S2 详情 详情
(II) 25060 4-methoxybenzyl 3-(chloromethyl)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate C16H16ClNO4S 详情 详情
(V) 25067 3-chloro-5-isoxazolecarbaldehyde C4H2ClNO2 详情 详情

合成路线2

该中间体在本合成路线中的序号:(IVc)

The cephalosporin was synthesized following the reaction pathway depicted in Scheme 25490201a: Protected 2-(2-aminothiazol-4-yl)-2-(alkoxy)iminoacetic acid ((Ia-c) was reacted with p-methoxybenzyl 7-amino-3-chloromethyl-cephaslosporonate (II) by a conventional method (POCl3, pyr / CH2Cl2. -5 C) to give the acylated product (IIIa-c). Product (IIIa-c) was then coverted to a phosponium salt (Iva-c) (PPh3, NaI / acetone, r.t.), followed by the reaction (NaHCO3(2N) / CH2Cl2, 0 C - r.t.) with a substituted isoxazole aldehyde (V) to afford the protected final product (Via-c). The aldehyde (V) was prepared by the sequential reduction-oxidation of the 1,3-dipolar cycloaddition product of methyl propiolate and the corresponding aldoxime. Deprotection, sodium salt formation and purification by reverse phase column chromatography (LiChrosorb(R) RP-18, 25% aq. MeOH) followed by frezee drying gave the final product as an amorphous white solid.

1 Choi, K.I.; Discovery of novel 3-isoxazolylvinylcephalosporins. Drugs Fut 1999, 24, 3, 287.
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) 25057 2-[2-(tritylamino)-1,3-thiazol-4-yl]-2-[(trityloxy)imino]acetic acid C43H33N3O3S 详情 详情
(Ib) 25058 2-(methoxyimino)-2-[2-(tritylamino)-1,3-thiazol-4-yl]acetic acid 64485-90-1 C25H21N3O3S 详情 详情
(Ic) 25059 2-[(cyclopentyloxy)imino]-2-[2-(tritylamino)-1,3-thiazol-4-yl]acetic acid C29H27N3O3S 详情 详情
(IIIa) 25061 4-methoxybenzyl 3-(chloromethyl)-8-oxo-7-([2-[2-(tritylamino)-1,3-thiazol-4-yl]-2-[(trityloxy)imino]acetyl]amino)-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate C59H48ClN5O6S2 详情 详情
(IIIb) 25062 4-methoxybenzyl 3-(chloromethyl)-7-([2-(methoxyimino)-2-[2-(tritylamino)-1,3-thiazol-4-yl]acetyl]amino)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate C41H36ClN5O6S2 详情 详情
(IIIc) 25063 4-methoxybenzyl 3-(chloromethyl)-7-([2-[(cyclopentyloxy)imino]-2-[2-(tritylamino)-1,3-thiazol-4-yl]acetyl]amino)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate C45H42ClN5O6S2 详情 详情
(IVa) 25064 [[2-[[(4-methoxybenzyl)oxy]carbonyl]-8-oxo-7-([2-[2-(tritylamino)-1,3-thiazol-4-yl]-2-[(trityloxy)imino]acetyl]amino)-5-thia-1-azabicyclo[4.2.0]oct-2-en-3-yl]methyl](triphenyl)phosphonium iodide C77H63IN5O6PS2 详情 详情
(IVb) 25065 [[2-[[(4-methoxybenzyl)oxy]carbonyl]-7-([2-(methoxyimino)-2-[2-(tritylamino)-1,3-thiazol-4-yl]acetyl]amino)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-en-3-yl]methyl](triphenyl)phosphonium iodide C59H51IN5O6PS2 详情 详情
(IVc) 25066 [(7-([2-[(cyclopentyloxy)imino]-2-[2-(tritylamino)-1,3-thiazol-4-yl]acetyl]amino)-2-[[(4-methoxybenzyl)oxy]carbonyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-en-3-yl)methyl](triphenyl)phosphonium iodide C63H57IN5O6PS2 详情 详情
(VIa) 25072 4-methoxybenzyl 3-[(E)-2-(3-methoxy-5-isoxazolyl)ethenyl]-8-oxo-7-([2-[2-(tritylamino)-1,3-thiazol-4-yl]-2-[(trityloxy)imino]acetyl]amino)-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate C64H52N6O8S2 详情 详情
(VIb) 25073 4-methoxybenzyl 7-([2-(methoxyimino)-2-[2-(tritylamino)-1,3-thiazol-4-yl]acetyl]amino)-3-[(E)-2-(3-methoxy-5-isoxazolyl)ethenyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate C46H40N6O8S2 详情 详情
(VIc) 25074 4-methoxybenzyl 7-([2-[(cyclopentyloxy)imino]-2-[2-(tritylamino)-1,3-thiazol-4-yl]acetyl]amino)-3-[(E)-2-(3-methoxy-5-isoxazolyl)ethenyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate C50H46N6O8S2 详情 详情
(II) 25060 4-methoxybenzyl 3-(chloromethyl)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate C16H16ClNO4S 详情 详情
(V) 25071 3-methoxy-5-isoxazolecarbaldehyde C5H5NO3 详情 详情
Extended Information