1,4,8,11-Tetraazacyclotetradecane → 4-((1,4,8,11-Tetraazacyclotetradec-1-yl)methyl)benzoic acid

HRID 507796노트

반응식

HRID 507796 반응식
[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

참가 물질

5

반응물 2

HCID 649641,4,8,11-TetraazacyclotetradecaneHCID 742344-(Chloromethyl)benzoic acid

생성물 1

HCID 1305774-((1,4,8,11-Tetraazacyclotetradec-1-yl)methyl)benzoic acid수율 66.6%

시약·촉매·용매 2

HCID 3939Lithium Hydroxide용매HCID 19096565Water ethanol용매

실험 절차

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%.

후처리

  1. temperatureThis mixture was thereafter refluxed vigorously
  2. customThen the solvent was removed at reduced pressure
  3. dissolutionthe residue was dissolved in 13 ml of water
  4. customThe aqueous solution obtained
  5. extractionwas then extracted with chloroform (10 times 3 ml)
  6. concentrationthe aqueous layer was concentrated at reduced pressure down to 2 ml
  7. customThe product as a white solid was precipitated
  8. additionby adding the solution of concentrated HCl and ethanol
  9. custompurified
  10. customby recrystallizing from ethanol/water/HCl

출처 및 근거

ORD 기록
ord-de8ef36700004b8288cb30135dc12e5f
출처 데이터셋
uspto-grants-2010_08
특허 번호
US07786292B2

반응 노트

불러오는 중…