Dichloromethane → HCID 53979746, Verbindung

HRID 443136Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 443136
[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) δ 0.96 (d, J=7 Hz, 3 H), 0.98 (d, J=7 Hz, 3 H), 2.13 (m, 1 H), 1.97 (s, 3 H), 3.11 (s, 6 H), 3.71 (s, 3 H), 4.07 (brd, J=16 Hz,. 1 H), 4.34 (dd, J=9, 5 Hz, 1 H), 4.42 (d, J=16 Hz, 1 H), 6.29 (s, 1 H), 6.37 (br, 1 H). 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-2f341971a1ab4dc0a78728784e4267c6
Quelldatensatz
uspto-grants-1999_04
Patentnummer
US05892052

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