diethyl 3-[[(4-methoxybenzyl)oxy][(4-methylphenyl)sulfonyl]amino]propylphosphonate -Drug Synthesis Database

【结构式】

【分子编号】39087

【品名】diethyl 3-[[(4-methoxybenzyl)oxy][(4-methylphenyl)sulfonyl]amino]propylphosphonate

【CA登记号】

【分子式】C₂₂H₃₂NO₇PS

【分子量】485.538382

【元素组成】C 54.42% H 6.64% N 2.88% O 23.07% P 6.38% S 6.6%

与该中间体有关的原料药合成路线共 2 条

合成路线1 合成路线2

合成路线1

该中间体在本合成路线中的序号：(VIII)

1) The condensation of 1,3-dibromopropane (II) with diethyl phosphonate (III) gives diethyl 3-bromopropylphosphonate (IV), which by reaction with butyraldehyde oxime (V) by means of sodium ethoxide in ethanol is converted to diethyl 3-(butylideneamino)propylphosphonate-N-oxide (VI). Finally, this compound is hydrolyzed with HCl in refluxing acetic acid to obtain compound (I). 2) The condensation of (IV) with N-(p-methoxybenzyloxy)-p-toluenesulfonamide (VII) by means of sodium ethoxide in ethanol gives diethyl 3-[N-methoxybenzyloxy)-N-tosylamino]propyl phosphonate (VIII), which is hydrolyzed with HCl in acetic acid to obtain compound (I). 3) The condensation of (IV) with methyl N-(benzyloxy)carbamate (IX) by means of sodium ethoxide in ethanol yields diethyl 3-(N-benzyloxy-N-methoxycarbonylamino)propylphosphonate (X), which is hydrolyzed with HCl in acetic acid to obtain compound (I). 4) The condensation of (IV) with hydroxylamine by means of NaOH in MeOH-H2O gives diethyl 3-(N-hydroxylamino)propylphosphonate (XI), which is hydrolyzed with HCl in acetic acid to obtain compound (I).

参考文献中间体

合成目标

【1】 Kuroda, Y.; et al.; US 4143135 .
【2】 Prous, J.R.; Castaner, J.; FR-31564. Drugs Fut 1980, 5, 5, 239.

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)	39088	3-(hydroxyamino)propylphosphonic acid		C₃H₁₀NO₄P	详情	详情
(II)	12581	1,3-Dibromopropane	109-64-8	C₃H₆Br₂	详情	详情
(III)	12714	diethyl phosphonate; diethyl phosphite	762-04-9	C₄H₁₁O₃P	详情	详情
(IV)	39080	diethyl 3-bromopropylphosphonate		C₇H₁₆BrO₃P	详情	详情
(V)	39081	butanal oxime	110-69-0	C₄H₉NO	详情	详情
(VI)	39084	(Z)butylidene[3-(diethoxyphosphoryl)propyl]ammoniumolate		C₁₁H₂₄NO₄P	详情	详情
(VII)	39083	N-[(4-methoxybenzyl)oxy]-4-methylbenzenesulfonamide		C₁₅H₁₇NO₄S	详情	详情
(VIII)	39087	diethyl 3-[[(4-methoxybenzyl)oxy][(4-methylphenyl)sulfonyl]amino]propylphosphonate		C₂₂H₃₂NO₇PS	详情	详情
(IX)	39082	methyl benzyloxycarbamate		C₉H₁₁NO₃	详情	详情
(X)	39086	diethyl 3-[(benzyloxy)(methoxycarbonyl)amino]propylphosphonate		C₁₆H₂₆NO₆P	详情	详情
(XI)	39085	diethyl 3-(hydroxyamino)propylphosphonate		C₇H₁₈NO₄P	详情	详情

合成路线2

该中间体在本合成路线中的序号：(VIII)

10) The condensation of diethyl phosphonate (III) with N-(p-methoxybenzyloxy)-N-(3-chloropropyl)-p-toluenesulfonamide (XXV) by means of NaH in refluxing benzene gives (VIII), which is hydrolyzed with HCl in acetic acid to obtain compound (I). 11) The condensation of (III) with N-(3-chloropropyl)-N-(benzyloxy)-p-toluenesulfonamide (XXVI) by means of NaH in refluxing benzene gives diethyl 3-(N-benzyloxy-N-tosylamino)propylphosphonate (XXVII), which is hydrolyzed with HCl in acetic acid to obtain compound (I). 12) By reaction of 3-bromopropylphosphonic acid (XXVIII) with hydroxylamine by means of sodium methoxide in MeOH to obtain compound (I).

参考文献中间体

合成目标

【1】 Kuroda, Y.; et al.; US 4143135 .
【2】 Prous, J.R.; Castaner, J.; FR-31564. Drugs Fut 1980, 5, 5, 239.

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)	39088	3-(hydroxyamino)propylphosphonic acid		C₃H₁₀NO₄P	详情	详情
(III)	12714	diethyl phosphonate; diethyl phosphite	762-04-9	C₄H₁₁O₃P	详情	详情
(VIII)	39087	diethyl 3-[[(4-methoxybenzyl)oxy][(4-methylphenyl)sulfonyl]amino]propylphosphonate		C₂₂H₃₂NO₇PS	详情	详情
(XXV)	39102	N-(3-chloropropyl)-N-[(4-methoxybenzyl)oxy]-4-methylbenzenesulfonamide		C₁₈H₂₂ClNO₄S	详情	详情
(XXVI)	39103	N-(benzyloxy)-N-(3-chloropropyl)-4-methylbenzenesulfonamide		C₁₇H₂₀ClNO₃S	详情	详情
(XXVII)	39104	diethyl 3-[(benzyloxy)[(4-methylphenyl)sulfonyl]amino]propylphosphonate		C₂₁H₃₀NO₆PS	详情	详情
(XXVIII)	39105	3-bromopropylphosphonic acid	1190-09-6	C₃H₈BrO₃P	详情	详情

Extended Information