Dichloromethane → HCID 53979746, Verbindung

HRID 742154Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 742154
[N:1]([C@@:4]([C:9]([OH:11])=[O:10])([CH:6]([CH3:8])[CH3:7])N)=[C:2]=[O:3].[CH3:12][N:13]([C:15]1[S:16][CH:17]=[C:18]([CH2:20][NH:21][CH3:22])[N:19]=1)[CH3:14].Cl[CH2:24]Cl>>[CH3:24][O:11][C:9](=[O:10])[C@H:4]([CH:6]([CH3:8])[CH3:7])[NH:1][C:2]([N:21]([CH3:22])[CH2:20][C:18]1[N:19]=[C:15]([N:13]([CH3:12])[CH3:14])[S:16][CH:17]=1)=[O:3]

Komponenten

4

Edukt 3

HCID 6344Dichloromethane2×HCID 187589612-(N,N-dimethylamino)-4-(((N-methyl)amino)methyl)thiazoleHCID 22856914alpha-isocyanato-L-valine

Produkt 1

HCID 53979746HCID 53979746, VerbindungAusbeute 34 %

Versuchsvorschrift

A solution of 741 mg (4.42 mmol) of α-isocyanato-L-valine in in 5 ml of dichloromethane was added to a solution of 720 mg (4.21 mmol) of 2-(N,N -dimethylamino)-4-(((N-methyl)amino)methyl)thiazole in 25 ml of dichloromethane. The resulting solution was stirred at ambient temperature for 16 h, partitioned between chloroform and aqueous NaHCO3, dried over Na2SO4, and concentrated in vacuo. The residue was purified by silica gel chromatography using 2% methanol in chloroform to provide 463 mg (34%) of the desired compound, Rf 0.25 (2% methanol in chloroform). NMR (CDCl3)δ0.96 (d, J=7 Hz, 3H), 0.98 (d, J=7 Hz, 3H), 2.13 (m, 1H), 2.97 (s, 3H), 3.11 (s, 6H), 3.71 (s, 3H), 4.07 (br d, J=16 Hz, 1H), 4.34 (dd, J=9, 5 Hz, 1H), 4.42 (d, J=16 Hz, 1H), 6.29 (s, 1H), 6.37 (br, 1H). Mass spectrum: (M+H)+ =329.

Aufarbeitung

  1. custompartitioned between chloroform and aqueous NaHCO3
  2. dry with materialdried over Na2SO4
  3. concentrationconcentrated in vacuo
  4. customThe residue was purified by silica gel chromatography

Quellen und Nachweise

ORD-Eintrag
ord-2b1f2352feaa4778800b0e128fdf0069
Quelldatensatz
uspto-grants-1996_09
Patentnummer
US05552558

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