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

HRID 276114

Reaktionsgleichung

Reaktionsgleichung von HRID 276114
C([O:5][C:6](=[O:44])[C@H:7]([CH2:37][C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1)[NH:8][C:9](=[O:36])[C@H:10]([CH2:28][CH2:29][C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)[NH:11][C:12](=[O:27])[CH:13]([S:17]CC1C=CC(OC)=CC=1)[CH2:14][CH2:15][CH3:16])(C)(C)C.C1(OC)C=CC=CC=1.C(Cl)(Cl)(Cl)Cl>ClCCl.C([O-])(=O)C.[Hg+2].C([O-])(=O)C>[SH:17][CH:13]([CH2:14][CH2:15][CH3:16])[C:12]([NH:11][C@H:10]([C:9]([NH:8][C@H:7]([C:6]([OH:44])=[O:5])[CH2:37][C:38]1[CH:39]=[CH:40][CH:41]=[CH:42][CH:43]=1)=[O:36])[CH2:28][CH2:29][C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)=[O:27]

Komponenten

6

Edukt 3

HCID 5943Carbon TetrachlorideHCID 7519AnisoleHCID 544815592-(4-methoxybenzylthio)-pentanoyl-(L)-homophenylalanyl-(L)-phenylalanine t-butyl ester

Produkt 1

HCID 155487402-mercapto-pentanoyl-(L)-homophenylalanyl-(L)-phenylalanineAusbeute 58,2 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 15337Mercuric acetateKatalysatorHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

Combine 2-(4-methoxybenzylthio)-pentanoyl-(L)-homophenylalanyl-(L)-phenylalanine t-butyl ester (0.20 g, 0.33 mmol), mercury (II) acetate (0.134 g, 0.42 mmol), and anisole (0.37 mL, 3.4 mmol) in dichloromethane (9 mL). Cool in an ice bath and degas by repeatedly applying vacuum and filling the vessel with nitrogen, Add trifluoroacetic acid (4 mL). After 1 hour, warm to ambient temperature. After 3 hours, purge with hydrogen sulfide (gas) for about 10 minutes. 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 (85 mg, 57%).

Aufarbeitung

  1. temperatureCool in an ice bath
  2. customdegas
  3. additionAdd trifluoroacetic acid (4 mL)
  4. waitAfter 3 hours
  5. custompurge with hydrogen sulfide (gas) for about 10 minutes
  6. filtrationFilter
  7. customevaporate in vacuo
  8. customto give a residue
  9. customevaporate in vacuo
  10. customto give a residue
  11. customTriturate the residue with hexane

Quellen und Nachweise

ORD-Eintrag
ord-5ae5529245274703a3c1f8b6e322927e
Quelldatensatz
uspto-grants-2002_03
Patentnummer
US06352976B1

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