【药物名称】BW-245C
化学结构式(Chemical Structure):
参考文献No.67140
标题:BW-245-C
作者:Serradell, M.N.; Blancafort, P.; Casta馿r, J.; Hillier, K.
来源:Drugs Fut 1982,7(6),380
合成路线图解说明:

The condensation of diethyl acetamidomalonate (I) with ethyl 7-bromoheptanoate (II) by means of sodium ethoxide in refluxing ethanol gives diethyl acetamido-(6-ethoxycarbonylhexyl)malonate (III), which is hydrolyzed and decarboxylated with refluxing concentrated HCl yielding 2-aminononanedioic acid (IV). This acid is esterified with SOCl2 and ethanol to the corresponding diethyl ester (V), which is condensed with vinyl cyclohexyl ketone (VI) to afford diethyl 2-[(3-oxo-3-cyclohexylpropyl)amino]nonanedioate (VII). The reaction of (VII) with potassium cyanate in ethanol-HCl gives the corresponding hydantoic ester (VIII), which is cyclized by heating at 100 C affording 5-(6-carboxyhexyl)-1-(3-cyclohexyl-3-oxopropyl)hydantoin (IX). Finally, this compound is reduced with NaBH4 in ethanol.

参考文献No.701294
标题:
作者:Caldwell, A.G.; Whittaker, N.
来源:US 4204068
合成路线图解说明:

The condensation of diethyl acetamidomalonate (I) with ethyl 7-bromoheptanoate (II) by means of sodium ethoxide in refluxing ethanol gives diethyl acetamido-(6-ethoxycarbonylhexyl)malonate (III), which is hydrolyzed and decarboxylated with refluxing concentrated HCl yielding 2-aminononanedioic acid (IV). This acid is esterified with SOCl2 and ethanol to the corresponding diethyl ester (V), which is condensed with vinyl cyclohexyl ketone (VI) to afford diethyl 2-[(3-oxo-3-cyclohexylpropyl)amino]nonanedioate (VII). The reaction of (VII) with potassium cyanate in ethanol-HCl gives the corresponding hydantoic ester (VIII), which is cyclized by heating at 100 C affording 5-(6-carboxyhexyl)-1-(3-cyclohexyl-3-oxopropyl)hydantoin (IX). Finally, this compound is reduced with NaBH4 in ethanol.

参考文献No.701295
标题:
作者:Caldwell, A.G.; Whittaker, N.
来源:BE 0876670
合成路线图解说明:

The condensation of diethyl acetamidomalonate (I) with ethyl 7-bromoheptanoate (II) by means of sodium ethoxide in refluxing ethanol gives diethyl acetamido-(6-ethoxycarbonylhexyl)malonate (III), which is hydrolyzed and decarboxylated with refluxing concentrated HCl yielding 2-aminononanedioic acid (IV). This acid is esterified with SOCl2 and ethanol to the corresponding diethyl ester (V), which is condensed with vinyl cyclohexyl ketone (VI) to afford diethyl 2-[(3-oxo-3-cyclohexylpropyl)amino]nonanedioate (VII). The reaction of (VII) with potassium cyanate in ethanol-HCl gives the corresponding hydantoic ester (VIII), which is cyclized by heating at 100 C affording 5-(6-carboxyhexyl)-1-(3-cyclohexyl-3-oxopropyl)hydantoin (IX). Finally, this compound is reduced with NaBH4 in ethanol.

参考文献No.800392
标题:Hydantoin prostaglandin analog, potemt and selective inhibitors of platelet aggregation
作者:Harris, C.J.; Stepney, R.; Caldwell, A.G.; Whittaker, N.
来源:J Chem Soc Chem Commun 1979,(13),561-562
合成路线图解说明:

The condensation of diethyl acetamidomalonate (I) with ethyl 7-bromoheptanoate (II) by means of sodium ethoxide in refluxing ethanol gives diethyl acetamido-(6-ethoxycarbonylhexyl)malonate (III), which is hydrolyzed and decarboxylated with refluxing concentrated HCl yielding 2-aminononanedioic acid (IV). This acid is esterified with SOCl2 and ethanol to the corresponding diethyl ester (V), which is condensed with vinyl cyclohexyl ketone (VI) to afford diethyl 2-[(3-oxo-3-cyclohexylpropyl)amino]nonanedioate (VII). The reaction of (VII) with potassium cyanate in ethanol-HCl gives the corresponding hydantoic ester (VIII), which is cyclized by heating at 100 C affording 5-(6-carboxyhexyl)-1-(3-cyclohexyl-3-oxopropyl)hydantoin (IX). Finally, this compound is reduced with NaBH4 in ethanol.

参考文献No.800393
标题:Heterocyclic prostaglandin analogs. Part 2. Hydantoins and other imidazole analogs
作者:Whittaker, N.; Harris, C.J.; Stepney, R.; Caldwell, A.G.
来源:J Chem Soc - Perkins Trans I 1980,1(2),495-505
合成路线图解说明:

The condensation of diethyl acetamidomalonate (I) with ethyl 7-bromoheptanoate (II) by means of sodium ethoxide in refluxing ethanol gives diethyl acetamido-(6-ethoxycarbonylhexyl)malonate (III), which is hydrolyzed and decarboxylated with refluxing concentrated HCl yielding 2-aminononanedioic acid (IV). This acid is esterified with SOCl2 and ethanol to the corresponding diethyl ester (V), which is condensed with vinyl cyclohexyl ketone (VI) to afford diethyl 2-[(3-oxo-3-cyclohexylpropyl)amino]nonanedioate (VII). The reaction of (VII) with potassium cyanate in ethanol-HCl gives the corresponding hydantoic ester (VIII), which is cyclized by heating at 100 C affording 5-(6-carboxyhexyl)-1-(3-cyclohexyl-3-oxopropyl)hydantoin (IX). Finally, this compound is reduced with NaBH4 in ethanol.

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