Trifluoromethanesulfonic acid → 1-[3-mercapto-2-(methylthio)propanoyl]-L-proline

HRID 46924Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 46924
C([O:5][C:6](=[O:28])[C@@H:7]1[CH2:11][CH2:10][CH2:9][N:8]1[C:12](=[O:27])[CH:13]([S:25][CH3:26])[CH2:14][S:15]CC1C=CC(OC)=CC=1)(C)(C)C.FC(F)(F)S(O)(=O)=O>ClCCl.C1(OC)C=CC=CC=1>[SH:15][CH2:14][CH:13]([S:25][CH3:26])[C:12]([N:8]1[CH2:9][CH2:10][CH2:11][C@H:7]1[C:6]([OH:28])=[O:5])=[O:27]

Komponenten

5

Edukt 2

HCID 62406Trifluoromethanesulfonic acidHCID 228056351-[3-(4-Methoxybenzylmercapto)-2-(methylthio)propanoyl]-L-proline tert-butyl ester

Produkt 1

HCID 228056361-[3-mercapto-2-(methylthio)propanoyl]-L-proline

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6344DichloromethaneLösungsmittelHCID 7519AnisoleLösungsmittel

Versuchsvorschrift

1-[3-(4-Methoxybenzylmercapto)-2-(methylthio)propanoyl]-L-proline tert-butyl ester (0.5 g.) is dissolved in a mixture of dichloromethane (2 ml.) and anisole (1.1 ml.) under a blanket of argon in an ice bath. Trifluoromethanesulfonic acid (1 g.) is added and the mixture is stirred at room temperature for thirty minutes. The solvent is removed in vacuo and the residue is distributed between water and ethyl acetate. The organic layer is washed six times with water, dried and concentrated to dryness in vacuo to yield 1-[3-mercapto-2-(methylthio)propanoyl]-L-proline.

Aufarbeitung

  1. customThe solvent is removed in vacuo
  2. washThe organic layer is washed six times with water
  3. customdried
  4. concentrationconcentrated to dryness in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-9363cde3754449c18c25c1640a2b922d
Quelldatensatz
uspto-grants-1979_11
Patentnummer
US04175199

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