6-Bromohexanoic acid → 1-(5-carboxypentyl)-4-(10,15,20-tri-4-pyridyl-21H,23H-porphin-5-yl)pyridinium bromide

HRID 65543

반응식

HRID 65543 반응식
[N:1]1[CH:6]=[CH:5][C:4]([C:7]2[C:8]3[NH:12][C:11]([C:13]([C:43]4[CH:48]=[CH:47][N:46]=[CH:45][CH:44]=4)=[C:14]4[N:42]=[C:17]([C:18]([C:36]5[CH:41]=[CH:40][N:39]=[CH:38][CH:37]=5)=[C:19]5[NH:35][C:22](=[C:23]([C:29]6[CH:34]=[CH:33][N:32]=[CH:31][CH:30]=6)[C:24]6[CH:25]=[CH:26][C:27]=2[N:28]=6)[CH:21]=[CH:20]5)[CH:16]=[CH:15]4)=[CH:10][CH:9]=3)=[CH:3][CH:2]=1.[Br:49][CH2:50][CH2:51][CH2:52][CH2:53][CH2:54][C:55]([OH:57])=[O:56]>C(Cl)(Cl)Cl.CO>[Br-:49].[C:55]([CH2:54][CH2:53][CH2:52][CH2:51][CH2:50][N+:46]1[CH:45]=[CH:44][C:43]([C:13]2[C:11]3[NH:12][C:8]([C:7]([C:4]4[CH:5]=[CH:6][N:1]=[CH:2][CH:3]=4)=[C:27]4[N:28]=[C:24]([C:23]([C:29]5[CH:30]=[CH:31][N:32]=[CH:33][CH:34]=5)=[C:22]5[NH:35][C:19](=[C:18]([C:36]6[CH:41]=[CH:40][N:39]=[CH:38][CH:37]=6)[C:17]6[CH:16]=[CH:15][C:14]=2[N:42]=6)[CH:20]=[CH:21]5)[CH:25]=[CH:26]4)=[CH:9][CH:10]=3)=[CH:48][CH:47]=1)([OH:57])=[O:56]

참가 물질

4

반응물 2

HCID 202106-Bromohexanoic acidHCID 1354117295,10,15,20-Tetra(4-pyridyl)porphyrin

생성물 1

HCID 1363321611-(5-carboxypentyl)-4-(10,15,20-tri-4-pyridyl-21H,23H-porphin-5-yl)pyridinium bromide수율 12.7%

시약·촉매·용매 1

HCID 21584188Chloroform methanol용매

실험 절차

180 mg of 5,10,15,20-tetra(4-pyridyl)-21H,23H-porphine are dissolved in 70 ml of chloroform/methanol (9:1), treated with 585 mg of 6-bromo-caproic acid and subsequently heated at reflux for 20 hours. The solution is then concentrated in vacuo to 5 to 10 ml and the product is precipitated by the addition of 250 ml of ether. The product is added to a 15 cm long silica column, whereupon the elution is carried out with 500 ml of chloroform/methanol (9:1), the starting zone is removed from the column and extracted with 1 liter of methanol and then with 1 liter of chloroform/methanol/water (2:7:1). The material obtained from the extracts is purified further by preparative thick-layer chromatography; eluent: chloroform/methanol/dimethylformamide/water (1:2:1:1). After scratching off, the main zone is extracted twice with 250 ml of methanol each time and twice with 250 ml of chloroform/methanol/water (2:7:1) each time. The product is finally re-precipitated a further four times. For this purpose, it is firstly dissolved in the smallest amount of methanol possible and then precipitated by the slow dropwise addition of 250 ml of chloroform. There are obtained 30 mg of 1-(5-carboxypentyl)-4-(10,15,20-tri-4-pyridyl-21H,23H-porphin-5-yl)pyridinium bromide.

후처리

  1. temperaturesubsequently heated
  2. temperatureat reflux for 20 hours
  3. concentrationThe solution is then concentrated in vacuo to 5 to 10 ml
  4. customthe product is precipitated by the addition of 250 ml of ether
  5. additionThe product is added to a 15 cm long silica column, whereupon the elution
  6. customthe starting zone is removed from the column
  7. extractionextracted with 1 liter of methanol
  8. customThe material obtained from the extracts
  9. customis purified further by preparative thick-layer chromatography
  10. extractionthe main zone is extracted twice with 250 ml of methanol each time
  11. customThe product is finally re-precipitated a further four times
  12. dissolutionFor this purpose, it is firstly dissolved in the smallest amount of methanol possible
  13. customprecipitated by the slow dropwise addition of 250 ml of chloroform

출처 및 근거

ORD 기록
ord-fdfccd3ba46b4460a05b3a357dda990c
출처 데이터셋
uspto-grants-1986_09
특허 번호
US04614723

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