Trifluoroacetic acid → N-[(1-Methylindole-2-Carbonyl)Valinyl]-3-Amino-4-Oxo-5-Fluoropentanoic Acid

HRID 1531727Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1531727
[CH3:1][N:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[C:3]1[C:11]([NH:13][C@H:14]([C:18]([NH:20][CH:21]([C:30](=[O:33])[CH2:31][F:32])[CH2:22][C:23]([O:25]C(C)(C)C)=[O:24])=[O:19])[CH:15]([CH3:17])[CH3:16])=[O:12].C1(OC)C=CC=CC=1.FC(F)(F)C(O)=O>C(Cl)Cl>[CH3:1][N:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[C:3]1[C:11]([NH:13][C@H:14]([C:18]([NH:20][CH:21]([C:30](=[O:33])[CH2:31][F:32])[CH2:22][C:23]([OH:25])=[O:24])=[O:19])[CH:15]([CH3:16])[CH3:17])=[O:12]

Komponenten

5

Edukt 3

HCID 6422Trifluoroacetic acidHCID 7519AnisoleHCID 86584009N-[(1-methylindole-2-carbonyl)valinyl]-3-amino-4-oxo-5-fluoropentanoic acid, t-butyl ester

Produkt 1

HCID 18335070N-[(1-Methylindole-2-Carbonyl)Valinyl]-3-Amino-4-Oxo-5-Fluoropentanoic AcidAusbeute 72,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

A solution of N-[(1-methylindole-2-carbonyl)valinyl]-3-amino-4-oxo-5-fluoropentanoic acid, t-butyl ester (19 mg, 0.041 mmol) and anisole (0.1 mL) in CH2Cl2 (1 mL) was treated with trifluoroacetic acid (0.5 mL) at room temperature. After 30 min the reaction mixture was concentrated and chased with methylene chloride. The crude residue was triturated with diethyl ether and the solid filtered to afford the title compound as a light brown solid (12 mg, 72% yield). TLC(AcOH:MeOH:CH2Cl2, 1:1:20): Rf=0.59. Mass Spectrum for C20H24FN3O5: [MH]+ 406, [MH]− 404.

Aufarbeitung

  1. concentrationAfter 30 min the reaction mixture was concentrated
  2. customThe crude residue was triturated with diethyl ether
  3. filtrationthe solid filtered

Quellen und Nachweise

ORD-Eintrag
ord-557e1d169404412dafe50af03a2d5b75
Quelldatensatz
uspto-grants-2001_03
Patentnummer
US06200969B1

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