dibutyl phosphonate -Drug Synthesis Database

【结构式】

【分子编号】39090

【品名】dibutyl phosphonate

【CA登记号】1809-19-4

【分子式】C₈H₁₉O₃P

【分子量】194.210822

【元素组成】C 49.48% H 9.86% O 24.71% P 15.95%

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：(XVI)

5) The condensation of 1-chloro-3-bromopropane (XII) with dibutyl phosphonate (XIII) affords dibutyl 3-chloropropylphosphonate (XIV), which by reaction with ethyl N-benzyloxycarbamate (A) is converted into dibutyl 3-(N-benzyloxy-N-ethoxycarbonylamino)propylphosphonate (XV). Finally, this compound is hydrolyzed with HCl in acetic acid to obtain compound (I). 6) The reaction of (XII) with diethyl phosphonate (III) yields diethyl 3-chloropropylphosphonate (XVI), which by condensation with ethyl N-ethoxycarbonyl-oxycarbamate (XVII) is converted into diethyl 3-(N-ethoxycarbonyloxy-N-ethoxycarbonylamino)propylphosphonate (XVIII). Finally, this compound 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
(A)	39093	ethyl benzyloxycarbamate		C₁₀H₁₃NO₃	详情	详情
(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
(XII)	10358	1-Bromo-3-chloropropane	109-70-6	C₃H₆BrCl	详情	详情
(XIII)	39089	diethyl 3-chloropropylphosphonate		C₇H₁₆ClO₃P	详情	详情
(XIV)	39091	dibutyl 3-chloropropylphosphonate		C₁₁H₂₄ClO₃P	详情	详情
(XV)	39095	dibutyl 3-[(benzyloxy)(ethoxycarbonyl)amino]propylphosphonate		C₂₁H₃₆NO₆P	详情	详情
(XVI)	39090	dibutyl phosphonate	1809-19-4	C₈H₁₉O₃P	详情	详情
(XVII)	39092	1-[([[(ethoxycarbonyl)amino]oxy]carbonyl)oxy]ethane		C₆H₁₁NO₅	详情	详情
(XVIII)	39094	4-ethoxy-8-(ethoxycarbonyl)-4,10-dioxo-3,9,11-trioxa-8-aza-4lambda(5)-phosphatridecane		C₁₃H₂₆NO₈P	详情	详情

合成路线2

该中间体在本合成路线中的序号：(XIII)

Isobutyl N-hydroxycarbamate (IX) was O-alkylated with 4-methoxybenzyl bromide (X) using NaOEt to give (XI). Subsequent N-alkylation with 1,3-dibromopropane (IV) produced bromide (XII), which was condensed with the sodium salt of dibutyl phosphonate (XIII) to furnish adduct (XIV). Acid hydrolysis of (XIV) then gave intermediate (VIII).

参考文献中间体

合成目标

【1】 Takeno, H.; Hemmi, K.; Hashimoto, M.; Kamiya, T. (Fujisawa Pharmaceutical Co., Ltd.); Hydroxyaminohydrocarbonphosphonic acids. DE 2733658; US 4182758; US 4206156 .

中间体序号	中间体编号	品名	CAS号	分子式	供应商	用于合成
(IV)	12581	1,3-Dibromopropane	109-64-8	C₃H₆Br₂	详情	详情
(VIII)	39088	3-(hydroxyamino)propylphosphonic acid		C₃H₁₀NO₄P	详情	详情
(IX)	42012	isobutyl hydroxycarbamate		C₅H₁₁NO₃	详情	详情
(X)	27490	1-(bromomethyl)-4-methoxybenzene		C₈H₉BrO	详情	详情
(XI)	42013	isobutyl (4-methoxybenzyl)oxycarbamate		C₁₃H₁₉NO₄	详情	详情
(XII)	42014	isobutyl 3-bromopropyl[(4-methoxybenzyl)oxy]carbamate		C₁₆H₂₄BrNO₄	详情	详情
(XIII)	39090	dibutyl phosphonate	1809-19-4	C₈H₁₉O₃P	详情	详情
(XIV)	42015	dibutyl 3-[(isobutoxycarbonyl)[(4-methoxybenzyl)oxy]amino]propylphosphonate		C₂₄H₄₂NO₇P	详情	详情

Extended Information