Cyclopropyl isothiocyanate → N-((1R) 1-benzyl-2-(3-cyclopropylthioureido)ethyl)-N-methylcarbamic acid tert-butylester

HRID 495850

Reaktionsgleichung

[CH:1]1([N:4]=[C:5]=[S:6])[CH2:3][CH2:2]1.[C:7]([O:11][C:12](=[O:25])[N:13]([C@@H:15]([CH2:23][NH2:24])[CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[CH3:14])([CH3:10])([CH3:9])[CH3:8]>ClCCl>[C:7]([O:11][C:12](=[O:25])[N:13]([C@H:15]([CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[CH2:23][NH:24][C:5]([NH:4][CH:1]1[CH2:3][CH2:2]1)=[S:6])[CH3:14])([CH3:10])([CH3:8])[CH3:9]

Komponenten

Reaktionsbedingungen

Temperatur: 0 °C

Versuchsvorschrift

At 0° C., cyclopropylisothiocyanate (0.32 ml) was added to a solution of N-((1R)-1-aminomethyl-2-phenylethyl)-N-methylcarbamic acid tert-butylester (410 mg, 1.6 mmol) in dichloromethane (4 ml). The reaction mixture was first stirred at 0° C. for 10 min, and successively for 2.5 h at room temperature. The solvent were removed in vacuo. The crude product was purified by flash chromatography on silica (50 g) using ethyl acetate/heptane as eluent to give 492 mg of N-((1R) 1-benzyl-2-(3-cyclopropylthioureido)ethyl)-N-methylcarbamic acid tert-butylester.

Aufarbeitung

waitsuccessively for 2.5 h at room temperature
customThe solvent were removed in vacuo
customThe crude product was purified by flash chromatography on silica (50 g)

Quellen und Nachweise

ORD-Eintrag: ord-5c7735bfbe884accbb567c13e25b8d3f
Quelldatensatz: uspto-grants-2005_09
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US06939880B2

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