Cesium carbonate → 2-(4-methoxybenzylthio)-pentanoyl-(L)-homophenylalanine methyl ester

HRID 276111

Reaktionsgleichung

Reaktionsgleichung von HRID 276111
[CH3:1][O:2][C:3](=[O:21])[C@H:4]([CH2:13][CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[NH:5][C:6](=[O:12])[CH:7](Br)[CH2:8][CH2:9][CH3:10].[CH3:22][O:23][C:24]1[CH:31]=[CH:30][C:27]([CH2:28][SH:29])=[CH:26][CH:25]=1.C(=O)([O-])[O-].[Cs+].[Cs+].CCCCCC.C(OCC)(=O)C>[I-].C([N+](CCCC)(CCCC)CCCC)CCC.CN(C)C=O>[CH3:1][O:2][C:3](=[O:21])[C@H:4]([CH2:13][CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[NH:5][C:6](=[O:12])[CH:7]([S:29][CH2:28][C:27]1[CH:30]=[CH:31][C:24]([O:23][CH3:22])=[CH:25][CH:26]=1)[CH2:8][CH2:9][CH3:10]

Komponenten

7

Edukt 4

HCID 10796Cesium carbonateHCID 804074-Methoxy-alpha-toluenethiolHCID 21226206Ethyl acetate hexane2×HCID 229508312-bromopentanoyl-(L)-homophenylalanine methyl ester

Produkt 1

HCID 229508282-(4-methoxybenzylthio)-pentanoyl-(L)-homophenylalanine methyl ester

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 67553Tetrabutylammonium IodideKatalysatorHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

Combine 2-bromopentanoyl-(L)-homophenylalanine methyl ester (3.6 g, 10 mmol), 4-methyoxybenzylmercaptan (3.48 mL, 25 mmol), and tetrabutylammonium iodide (about 50 mg) in dimethylformamide (10 mL). Degas by repeatedly applying vacuum and filling the vessel with nitrogen. Add cesium carbonate (4.10 g, 12.5 mmol). After 15 hours, partition the reaction mixture between water and methyl t-butyl ether, saturate the aqueous layer with sodium chloride. Extract the aqueous layer with brine, dry over Na2SO4, filter, and evaporate in vacuo to give a residue. Chromatograph the residue on silica gel eluting sequentially with 4/1 hexane/ethyl acetate and then 2.5/1 hexane/ethyl acetate to give the title compound: Rf=0.44 (silica gel, 2.5/1 hexane/ethyl acetate).

Aufarbeitung

  1. customDegas
  2. custompartition the reaction mixture between water and methyl t-butyl ether
  3. concentrationsaturate the aqueous layer with sodium chloride
  4. extractionExtract the aqueous layer with brine
  5. dry with materialdry over Na2SO4
  6. filtrationfilter
  7. customevaporate in vacuo
  8. customto give a residue

Quellen und Nachweise

ORD-Eintrag
ord-d1385ca9dc824c218ae0cd8094c64e04
Quelldatensatz
uspto-grants-2002_03
Patentnummer
US06352976B1

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