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【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

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.

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.

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