Carbon Tetrachloride → N,N'-di-(2-methylphenethyl)-2-((S)-2-mercapto-3-phenylpropionylamino)malonamide

HRID 2269828Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2269828
[CH3:1][C:2]1[CH:46]=[CH:45][CH:44]=[CH:43][C:3]=1[CH2:4][CH2:5][NH:6][C:7](=[O:42])[CH:8]([NH:21][C:22](=[O:41])[C@@H:23]([S:31]CC1C=CC(OC)=CC=1)[CH2:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)[C:9]([NH:11][CH2:12][CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[CH3:20])=[O:10].C1(OC)C=CC=CC=1.C(Cl)(Cl)(Cl)Cl>ClCCl.C([O-])(=O)C.[Hg+2].C([O-])(=O)C>[CH3:1][C:2]1[CH:46]=[CH:45][CH:44]=[CH:43][C:3]=1[CH2:4][CH2:5][NH:6][C:7](=[O:42])[CH:8]([NH:21][C:22](=[O:41])[C@@H:23]([SH:31])[CH2:24][C:25]1[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=1)[C:9]([NH:11][CH2:12][CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[CH3:20])=[O:10]

Komponenten

6

Edukt 3

HCID 5943Carbon TetrachlorideHCID 7519AnisoleHCID 20713092N,N'-di-(2-methylphenethyl)-2-((S)-2-(p-methoxybenzylmercapto)-3-phenylpropionylamino)malonamide

Produkt 1

HCID 20713091N,N'-di-(2-methylphenethyl)-2-((S)-2-mercapto-3-phenylpropionylamino)malonamide

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 15337Mercuric acetateKatalysatorHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

Combine of N,N′-di-(2-methylphenethyl)-2-((S)-2-(p-methoxybenzylmercapto)-3-phenylpropionylamino)malonamide (0.175 g, 0.274 mmol), mercury (II) acetate (0.108 g, 0.34 mmol), and anisole (0.3 mL) in dichloromethane (10 mL). Cool in an ice bath and degas by repeatedly applying vacuum and filling the vessel with nitrogen. Add trifluoroacetic acid (4 mL). After 3 hours, purge with hydrogen sulfide (gas) for about 10 minutes. Filter and evaporate in vacuo to give a residue. Combine the residue with carbon tetrachloride and evaporate in vacuo to remove most of the trifluoroacetic acid. Chromatograph the residue on silica gel eluting with 1/2 ethyl acetate/hexane and then 1/1 ethyl acetate/hexane to give the title compound.

Aufarbeitung

  1. temperatureCool in an ice bath
  2. customdegas
  3. custompurge with hydrogen sulfide (gas) for about 10 minutes
  4. filtrationFilter
  5. customevaporate in vacuo
  6. customto give a residue
  7. customevaporate in vacuo
  8. customto remove most of the trifluoroacetic acid

Quellen und Nachweise

ORD-Eintrag
ord-a27b40b9e74048ed9c7c06e1337060dc
Quelldatensatz
uspto-grants-2001_12
Patentnummer
US06329550B1

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