Carbon Tetrachloride → 2-mercapto-pentanoyl-(L)-homophenylalanyl-(L)-phenylalanine-N-methyl amide

HRID 276117

Reaktionsgleichung

Reaktionsgleichung von HRID 276117
[CH3:1][NH:2][C:3](=[O:41])[C@H:4]([CH2:34][C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1)[NH:5][C:6](=[O:33])[C@H:7]([CH2:25][CH2:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)[NH:8][C:9](=[O:24])[CH:10]([S:14]CC1C=CC(OC)=CC=1)[CH2:11][CH2:12][CH3:13].C1(OC)C=CC=CC=1.C(Cl)(Cl)(Cl)Cl>ClCCl.C([O-])(=O)C.[Hg+2].C([O-])(=O)C>[CH3:1][NH:2][C:3](=[O:41])[C@H:4]([CH2:34][C:35]1[CH:36]=[CH:37][CH:38]=[CH:39][CH:40]=1)[NH:5][C:6](=[O:33])[C@H:7]([CH2:25][CH2:26][C:27]1[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=1)[NH:8][C:9](=[O:24])[CH:10]([SH:14])[CH2:11][CH2:12][CH3:13]

Komponenten

6

Edukt 3

HCID 5943Carbon TetrachlorideHCID 7519AnisoleHCID 867578252-(4-methoxybenzylthio)-pentanoyl-(L)-homophenylalanyl-(L)-phenylalanine N-methyl amide

Produkt 1

HCID 598787442-mercapto-pentanoyl-(L)-homophenylalanyl-(L)-phenylalanine-N-methyl amideAusbeute 80,5 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 15337Mercuric acetateKatalysatorHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

Combine 2-(4-methoxybenzylthio)-pentanoyl-(L)-homophenylalanyl-(L)-phenylalanine N-methyl amide (0.26 g, 0.45 mmol), mercury (II) acetate (0.156 g, 0.49 mmol), and anisole (0.49 mL, 4.5 mmol) in dichloromethane (10 mL). Cool in an ice bath and degas by repeatedly applying vacuum and filling the vessel with nitrogen. Add trifluoroacetic acid (2 mL). After 3 hours, filter and evaporate in vacuo to give a residue. Repeatedly, combine the residue and carbon tetrachloride and evaporate in vacuo to give a residue. Triturate the residue with hexane to give the title compound as a solid (165 mg, 80.4%).

Aufarbeitung

  1. temperatureCool in an ice bath
  2. customdegas
  3. filtrationfilter
  4. customevaporate in vacuo
  5. customto give a residue
  6. customevaporate in vacuo
  7. customto give a residue
  8. customTriturate the residue with hexane

Quellen und Nachweise

ORD-Eintrag
ord-27473199c8ff43b1ac82c772cd020e0b
Quelldatensatz
uspto-grants-2002_03
Patentnummer
US06352976B1

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