Phosgene → 1-{4'-[4-(3-Benzyl-2-oxo-oxazolidin-5-yl)-3-methyl-isoxazol-5-yl]-biphenyl-4-yl}-cyclopropanecarboxylic acid ethyl ester

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Reaktionsgleichung

[CH2:1]([O:3][C:4]([C:6]1([C:9]2[CH:14]=[CH:13][C:12]([C:15]3[CH:20]=[CH:19][C:18]([C:21]4[O:25][N:24]=[C:23]([CH3:26])[C:22]=4[CH:27]([OH:37])[CH2:28][NH:29][CH2:30][C:31]4[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=4)=[CH:17][CH:16]=3)=[CH:11][CH:10]=2)[CH2:8][CH2:7]1)=[O:5])[CH3:2].C(N(CC)CC)C.[C:45](Cl)(Cl)=[O:46].CCOC(C)=O>C1(C)C=CC=CC=1>[CH2:1]([O:3][C:4]([C:6]1([C:9]2[CH:10]=[CH:11][C:12]([C:15]3[CH:20]=[CH:19][C:18]([C:21]4[O:25][N:24]=[C:23]([CH3:26])[C:22]=4[CH:27]4[O:37][C:45](=[O:46])[N:29]([CH2:30][C:31]5[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=5)[CH2:28]4)=[CH:17][CH:16]=3)=[CH:13][CH:14]=2)[CH2:8][CH2:7]1)=[O:5])[CH3:2]

Komponenten

Reaktionsbedingungen

Temperatur: 0 °C

Versuchsvorschrift

1-{4′-[4-(2-Benzylamino-1-hydroxy-ethyl)-3-methyl-isoxazol-5-yl]-biphenyl-4-yl}-cyclopropanecarboxylic acid ethyl ester (0.190 g, 0.38 mmol) was dissolved in toluene (4 mL) then placed under N2 atmosphere at 0° C. Triethylamine (0.159 mL, 1.14 mmol) and phosgene (1.9M in toluene, 0.201 mL, 0.38 mmol) were added and the reaction stirred at 0° C. After two hours an additional portion of each of triethylamine (0.160 mL) and phosgene (0.200 mL) were added and the reaction stirred an additional 20 minutes. The reaction was submitted to standard workup procedures and silica gel chromatography (0-40% EtOAc in hexanes) to yield the title compound.

Aufarbeitung

customthen placed under N2 atmosphere at 0° C
stirringthe reaction stirred an additional 20 minutes

Quellen und Nachweise

ORD-Eintrag: ord-29a098f6d46e4a59b76f6643c648f7cc
Quelldatensatz: uspto-grants-2014_03
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US08664220B2

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