Trifluoroacetic acid → (2S)-2-(3-benzyl-2-oxo-1-imidazolidinyl)-3,3-dimethylbutanoic acid

HRID 1174300Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1174300
[CH2:1]([N:8]1[CH2:12][CH2:11][N:10]([C@@H:13]([C:21]([CH3:24])([CH3:23])[CH3:22])[C:14]([O:16]C(C)(C)C)=[O:15])[C:9]1=[O:25])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.FC(F)(F)C(O)=O>ClCCl>[CH2:1]([N:8]1[CH2:12][CH2:11][N:10]([C@@H:13]([C:21]([CH3:23])([CH3:22])[CH3:24])[C:14]([OH:16])=[O:15])[C:9]1=[O:25])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Komponenten

4

Edukt 2

HCID 6422Trifluoroacetic acidHCID 67405684tert-butyl(2S)-2-(3-benzyl-2-oxoimidazolidin-1-yl)-3,3-dimethylbutanoate

Produkt 1

HCID 42626247(2S)-2-(3-benzyl-2-oxo-1-imidazolidinyl)-3,3-dimethylbutanoic acid

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a solution of the product of Example 111-5 in dichloromethane (1.5 L) was added triflouroacetic acid (810 mL). The mixture was stirred at room temperature for 3 hours and concentrated. The residue was chased with heptanes (4×500 mL). The product was partitioned between dichloromethane (1.5 L) and 5% KH2PO4 (1.1 L). The organic layer was washed with 5% KH2PO4 (900 mL) and brine (900 mL), and concentrated. A solution of the residue in dichloromethane (500 mL) was dried over MgSO4, filtered and concentrated. The residue was recrystallized twice from isopropyl alcohol/water to afford the title compound. 1H NMR (DMSO-d6): δ 7.2-7.4(m, 5H), 4.28(d, 2H), 4.21(s, 1H), 3.47-3.64(m, 2H), 3.08-3.2(m, 2H), 1.0(s, 9H).

Aufarbeitung

  1. concentrationconcentrated
  2. customThe product was partitioned between dichloromethane (1.5 L) and 5% KH2PO4 (1.1 L)
  3. washThe organic layer was washed with 5% KH2PO4 (900 mL) and brine (900 mL)
  4. concentrationconcentrated
  5. dry with materialA solution of the residue in dichloromethane (500 mL) was dried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe residue was recrystallized twice from isopropyl alcohol/water

Quellen und Nachweise

ORD-Eintrag
ord-0977f4b22d4244ef98751220588fc9e1
Quelldatensatz
uspto-grants-2010_11
Patentnummer
US07834043B2

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