(4-Isopropylthiazol-2-yl)methanol → N-((4-Isopropyl-2-thiazolyl)methoxycarbonyl)valine Methyl Ester

HRID 52713

Reaktionsgleichung

Reaktionsgleichung von HRID 52713
[CH3:1][O:2][C:3](=[O:12])[C@:4]([N:9]=[C:10]=[O:11])([CH:6]([CH3:8])[CH3:7])N.[OH:13][CH2:14][C:15]1[S:16][CH:17]=[C:18]([CH:20]([CH3:22])[CH3:21])[N:19]=1>C(Cl)(Cl)Cl>[CH3:1][O:2][C:3](=[O:12])[C@H:4]([CH:6]([CH3:8])[CH3:7])[NH:9][C:10]([O:13][CH2:14][C:15]1[S:16][CH:17]=[C:18]([CH:20]([CH3:22])[CH3:21])[N:19]=1)=[O:11]

Komponenten

4

Edukt 2

HCID 10678505(4-Isopropylthiazol-2-yl)methanolHCID 22845662a-Isocyanato-valine methyl ester

Produkt 1

HCID 10781572N-((4-Isopropyl-2-thiazolyl)methoxycarbonyl)valine Methyl EsterAusbeute 52,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6212ChloroformLösungsmittel

Versuchsvorschrift

A solution of 1.4 mmol of α-isocyanato-valine methyl ester and 0.22 g (1.4 mmol) of 2-(hydroxymethyl)-4-isopropylthiazole in 10 ml of chloroform was heated at reflux for 3 h. After being allowed to cool, the solvent was removed in vacuo, and the residue was purified by silica gel chromatography using 2% methanol in chloroform to provide 0.23 g (52%) of the desired compound (Rf 0.54, 5% methanol in dichloromethane). NMR 1H NMR (DMSO-d6) δ0.87 (d, J=7 Hz, 3H), 0.88 (d, J=7 Hz, 3H), 1.23 (d, J=7 Hz, 6H), 2.04 (octet, J=7 Hz, 1H), 3.01 (heptet, J=7 Hz, 1H), 3.73 (s, 3H), 3.94 (dd, J=8, 6 Hz, 1H), 5.26 (AA', 2H), 7.28 (s, 1H), 7.92 (d, J=8 Hz, 1H). Mass spectrum: (M+H)+ =315.

Aufarbeitung

  1. temperatureat reflux for 3 h
  2. temperatureto cool
  3. customthe solvent was removed in vacuo
  4. customthe residue was purified by silica gel chromatography

Quellen und Nachweise

ORD-Eintrag
ord-4389567189584570bb549b4851d0b8aa
Quelldatensatz
uspto-grants-1997_04
Patentnummer
US05616720

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