反応式
[NH:1]1[CH2:14][CH2:13][CH2:12][NH:11][CH2:10][CH2:9][NH:8][CH2:7][CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1.Cl[CH2:16][C:17]1[CH:25]=[CH:24][C:20]([C:21]([OH:23])=[O:22])=[CH:19][CH:18]=1>C(O)C.O.[Li+].[OH-]>[N:1]1([CH2:16][C:17]2[CH:25]=[CH:24][C:20]([C:21]([OH:23])=[O:22])=[CH:19][CH:18]=2)[CH2:14][CH2:13][CH2:12][NH:11][CH2:10][CH2:9][NH:8][CH2:7][CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1参加物
実験手順
To solution of Cyclam (0.913 g, 4.5 mmol) dissolved in a mixture of ethanol:water (5:1 by vol.) (18 ml) was added a solution of 4-chloromethylbenzoic acid (0.157 g, 0.92 mmol) in aqueous LiOH (53 mg in 4 ml of water). This mixture was thereafter refluxed vigorously with stirring for 5 hours. Then the solvent was removed at reduced pressure, and the residue was dissolved in 13 ml of water. The aqueous solution obtained was then extracted with chloroform (10 times 3 ml) and the aqueous layer was concentrated at reduced pressure down to 2 ml. The product as a white solid was precipitated by adding the solution of concentrated HCl and ethanol and purified by recrystallizing from ethanol/water/HCl to yield 0.205 g of the title compound. According to the LC-MS, the assay of 4-(1,4,8,11-tetraazacyclotetradec-1-ylmethyl)-benzoic acid hydrochloride was >95%.
後処理
- temperatureThis mixture was thereafter refluxed vigorously
- customThen the solvent was removed at reduced pressure
- dissolutionthe residue was dissolved in 13 ml of water
- customThe aqueous solution obtained
- extractionwas then extracted with chloroform (10 times 3 ml)
- concentrationthe aqueous layer was concentrated at reduced pressure down to 2 ml
- customThe product as a white solid was precipitated
- additionby adding the solution of concentrated HCl and ethanol
- custompurified
- customby recrystallizing from ethanol/water/HCl
出典と根拠
- ORDレコード
- ord-de8ef36700004b8288cb30135dc12e5f
- 出典データセット
- uspto-grants-2010_08
- 特許番号
- US07786292B2
関連ノート
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