1,2-Dichloroethane → HCID 19437233, Verbindung

HRID 1728326Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1728326
[C:1]([O:5][C:6]([NH:8][C:9]([CH3:17])([CH2:13][CH2:14][CH2:15][OH:16])[C:10](O)=[O:11])=[O:7])([CH3:4])([CH3:3])[CH3:2].C(Cl)CCl>CN(C=O)C>[C:1]([O:5][C:6]([NH:8][C:9]1([CH3:17])[CH2:13][CH2:14][CH2:15][O:16][C:10]1=[O:11])=[O:7])([CH3:4])([CH3:3])[CH3:2]

Komponenten

4

Edukt 2

HCID 111,2-DichloroethaneHCID 19437231N-[(1,1-Dimethylethoxy)carbonyl]-5-hydroxy-2-methylnorvaline

Produkt 1

HCID 19437233HCID 19437233, VerbindungAusbeute 31,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

2-(t-Butyloxycarbonyl)amino-2-methyl-5-hydroxypentanoic acid (3.0 g, 0.012 mol) and EDC (2.56 g, 0.013 mol) were dissolved in DMF (20 mL) and stirred at ambient temperature for 18 h. The reaction mixture was concentrated to dryness, and the residue was partitioned between EtOAc (30 mL)-H2O (30 mL), the organic layer separated, washed with brine and dried (Na2SO4). Filtration, concentration, and chromatography (SiO2, EtOAc: hexane, 1:3) gave 0.86 g (31%) of the title compound. 1H NMR (CDCl3) δ 5.1 (br s, 1H), 4.35-4.55 (m, 2H), 2.49-2.64 (m, 1H), 1.78-2.1 (m, 3H), 1.45 (s, 3H), 1.41 (s, 9H).

Aufarbeitung

  1. concentrationThe reaction mixture was concentrated to dryness
  2. customthe residue was partitioned between EtOAc (30 mL)-H2O (30 mL)
  3. customthe organic layer separated
  4. washwashed with brine
  5. dry with materialdried (Na2SO4)
  6. filtrationFiltration, concentration, and chromatography (SiO2, EtOAc: hexane, 1:3)

Quellen und Nachweise

ORD-Eintrag
ord-d70374afbedb461fb924002737727769
Quelldatensatz
uspto-grants-1994_07
Patentnummer
US05326773

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