benzyl 1-(2-cyanoethyl)-2-propenylcarbamate -Drug Synthesis Database

【结构式】

【分子编号】59992

【品名】benzyl 1-(2-cyanoethyl)-2-propenylcarbamate

【CA登记号】

【分子式】C₁₄H₁₆N₂O₂

【分子量】244.29332

【元素组成】C 68.83% H 6.6% N 11.47% O 13.1%

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：(X)

The reaction of 3-aminotetrahydrofuran-2-one (I) with benzyloxycarbonyl chloride (II) and TEA in chloroform gives the carbamate (III), which is reduced to the lactol (IV) by means of DIBAL in toluene. It has been observed that lactol (IV) is in equilibrium with its tautomeric open chain aldehydic form.(V). The reaction of (IV)??(V) with phosphonium bromide (VI) by means of Bu-Li in THF yields 3-amino-4-penten-1-ol (VII), which is reprotected with benzyloxycarbonyl chloride (II) and TEA to afford the carbamate (VIII). The reaction of (VIII) with CBr4 and PPh3 in dichloromethane provides the pentenyl bromide (IX), which is treated with LiCN in THF to give 4-(benzyloxycarbonylamino)-5-hexenenitrile (X). Finally this compound is hydrolyzed with conc. HCl to yield the target 4-amino-5-hexenoic acid.

参考文献中间体

合成目标

【1】 Zhang, Z.; Ding, Y.S.; Studenov, A.R.; Gerasimov, M.R.; Ferrieri, R.A.; Novel synthesis of [1-11C]gamma-vinyl-gamma-aminobutyric acid ([1-11C]GVG) for pharmacokinetic studies of addiction treatment. J Label Compd Radiopharm 2002, 45, 3, 199.

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)	59984	3-aminodihydro-2(3H)-furanone		C₄H₇NO₂	详情	详情
(II)	10101	Benzyloxycarbonyl chloride; Benzyl chloroformate; 1-[[(Chlorocarbonyl)oxy]methyl]benzene	501-53-1	C₈H₇ClO₂	详情	详情
(III)	59985	benzyl 2-oxotetrahydro-3-furanylcarbamate		C₁₂H₁₃NO₄	详情	详情
(IV)	59986	benzyl 2-hydroxytetrahydro-3-furanylcarbamate		C₁₂H₁₅NO₄	详情	详情
(V)	59987	benzyl 1-formyl-3-hydroxypropylcarbamate		C₁₂H₁₅NO₄	详情	详情
(VI)	59988	methyl(triphenyl)phosphonium		C₁₉H₁₈P	详情	详情
(VII)	59989	3-amino-4-penten-1-ol		C₅H₁₁NO	详情	详情
(VIII)	59990	benzyl 1-(2-hydroxyethyl)-2-propenylcarbamate		C₁₃H₁₇NO₃	详情	详情
(IX)	59991	benzyl 1-(2-bromoethyl)-2-propenylcarbamate		C₁₃H₁₆BrNO₂	详情	详情
(X)	59992	benzyl 1-(2-cyanoethyl)-2-propenylcarbamate		C₁₄H₁₆N₂O₂	详情	详情

合成路线2

该中间体在本合成路线中的序号：(X)

The reaction of 3-aminotetrahydrofuran-2-one (I) with benzyloxycarbonyl chloride (II) and TEA in chloroform gives the carbamate (III), which is reduced to the lactol (IV) by means of DIBAL in toluene. It has been observed that lactol (IV) is in equilibrium with its tautomeric open chain aldehydic form (V). The reaction of (IV)??(V) with phosphonium bromide (VI) by means of Bu-Li in THF yields 3-amino-4-penten-1-ol (VII), which is reprotected with benzyloxycarbonyl chloride (II) and TEA to afford the carbamate (VIII). The reaction of (VIII) with CBr4 and PPh3 in dichloromethane provides the pentenyl bromide (IX), which is treated with 11C labeled LiCN in THF to give 4-(benzyloxycarbonylamino)-5-hexenenitrile (X). Finally this compound is hydrolyzed with conc. HCl to yield the target 11C labeled 4-amino-5-hexenoic acid.

参考文献中间体

合成目标

【1】 Zhang, Z.; Ding, Y.S.; Studenov, A.R.; Gerasimov, M.R.; Ferrieri, R.A.; Novel synthesis of [1-11C]gamma-vinyl-gamma-aminobutyric acid ([1-11C]GVG) for pharmacokinetic studies of addiction treatment. J Label Compd Radiopharm 2002, 45, 3, 199.

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)	59984	3-aminodihydro-2(3H)-furanone		C₄H₇NO₂	详情	详情
(II)	10101	Benzyloxycarbonyl chloride; Benzyl chloroformate; 1-[[(Chlorocarbonyl)oxy]methyl]benzene	501-53-1	C₈H₇ClO₂	详情	详情
(III)	59985	benzyl 2-oxotetrahydro-3-furanylcarbamate		C₁₂H₁₃NO₄	详情	详情
(IV)	59986	benzyl 2-hydroxytetrahydro-3-furanylcarbamate		C₁₂H₁₅NO₄	详情	详情
(V)	59987	benzyl 1-formyl-3-hydroxypropylcarbamate		C₁₂H₁₅NO₄	详情	详情
(VI)	59988	methyl(triphenyl)phosphonium		C₁₉H₁₈P	详情	详情
(VII)	59989	3-amino-4-penten-1-ol		C₅H₁₁NO	详情	详情
(VIII)	59990	benzyl 1-(2-hydroxyethyl)-2-propenylcarbamate		C₁₃H₁₇NO₃	详情	详情
(IX)	59991	benzyl 1-(2-bromoethyl)-2-propenylcarbamate		C₁₃H₁₆BrNO₂	详情	详情
(X)	59992	benzyl 1-(2-cyanoethyl)-2-propenylcarbamate		C₁₄H₁₆N₂O₂	详情	详情
(X)	59993	benzyl 1-(2-cyanoethyl)-2-propenylcarbamate		C₁₄H₁₆N₂O₂	详情	详情

Extended Information