3-(2,3-dichloro-phenoxy)-4-{(1S,3S)-3-ethoxy-1-[1-(2-hydroxy-2-methyl-propyl)-1H-pyrazol-3-ylcarbamoyl]-butylamino}-but-2-enoic acid ethyl ester → HCID 44252315, Verbindung

HRID 19046

Reaktionsgleichung

Reaktionsgleichung von HRID 19046
C(O[C:4](=[O:38])[CH:5]=[C:6]([O:29][C:30]1[CH:35]=[CH:34][CH:33]=[C:32]([Cl:36])[C:31]=1[Cl:37])[CH2:7][NH:8][C@H:9]([C:16](=[O:28])[NH:17][C:18]1[CH:22]=[CH:21][N:20]([CH2:23][C:24]([OH:27])([CH3:26])[CH3:25])[N:19]=1)[CH2:10][C@@H:11]([O:13][CH2:14][CH3:15])[CH3:12])C>O1CCCC1>[OH:27][C:24]([CH3:25])([CH3:26])[CH2:23][N:20]1[CH:21]=[CH:22][C:18]([NH:17][C:16](=[O:28])[C@@H:9]([N:8]2[CH2:7][C:6]([O:29][C:30]3[CH:35]=[CH:34][CH:33]=[C:32]([Cl:36])[C:31]=3[Cl:37])=[CH:5][C:4]2=[O:38])[CH2:10][C@@H:11]([O:13][CH2:14][CH3:15])[CH3:12])=[N:19]1

Komponenten

3

Edukt 1

HCID 675042483-(2,3-dichloro-phenoxy)-4-{(1S,3S)-3-ethoxy-1-[1-(2-hydroxy-2-methyl-propyl)-1H-pyrazol-3-ylcarbamoyl]-butylamino}-but-2-enoic acid ethyl ester

Produkt 1

HCID 44252315HCID 44252315, VerbindungAusbeute 36,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
160 °C

Versuchsvorschrift

3-(2,3-Dichloro-phenoxy)-4-{(1S,3S)-3-ethoxy-1-[1-(2-hydroxy-2-methyl-propyl)-1H-pyrazol-3-ylcarbamoyl]-butylamino}-but-2-enoic acid ethyl ester (120 mg) was dissolved in tetrahydrofuran (2 mL). The sealed tube was heated in a microwave at 160° C. for 4 h. The resulting solution was concentrated and the residue was purified by reverse phase column chromatography (acetonitrile in water 25% to 100%) to give (2S,4S)-2-[4-(2,3-dichloro-phenoxy)-2-oxo-2,5-dihydro-pyrrol-1-yl]-4-ethoxy-pentanoic acid [1-(2-hydroxy-2-methyl-propyl)-1H-pyrazol-3-yl]-amide (40 mg) as a white powder: HR-ES-MS m/z calculated for C24H30Cl2N4O5 [M+H]+ 525.1666, observed 525.1669; 1H NMR (300 MHz, CDCl3) δ ppm 1.14 (br. s., 6H), 1.19-1.30 (m, 6H), 1.88-2.09 (m, 1H), 2.18 (ddd, J=14.7, 9.3, 5.9 Hz, 1H), 3.30-3.46 (m, 1H), 3.54 (br. s., 1H), 3.61-3.77 (m, 1H), 3.94 (s, 2H), 4.14 (d, J=17.8 Hz, 1H), 4.47 (d, J=17.8 Hz, 1H), 4.92 (s, 1H), 5.01 (t, J=6.2 Hz, 1H), 6.68 (d, J=1.5 Hz, 1H), 7.16-7.33 (m, 4H), 7.42 (d, J=7.8 Hz, 1H), 9.35 (br. s., 1H).

Aufarbeitung

  1. concentrationThe resulting solution was concentrated
  2. customthe residue was purified by reverse phase column chromatography (acetonitrile in water 25% to 100%)

Quellen und Nachweise

ORD-Eintrag
ord-f4afa48db1a246a9b0296b29ac2b75a1
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07741327B2

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