Triethylamine → (13E)-(6RS,9alpha,11alpha,15S)-6,9-Epithio-11,15-dihydroxyprost-13-enoic acid 4-semicarbazonotolyl ester
Reaktionsgleichung
[S:1]1[C@H:12]2[CH2:13][C@@H:14]([OH:25])[C@H:15](/[CH:16]=[CH:17]/[C@@H:18]([OH:24])[CH2:19][CH2:20][CH2:21][CH2:22][CH3:23])[C@H:11]2[CH2:10][CH:2]1[CH2:3][CH2:4][CH2:5][CH2:6][C:7]([OH:9])=[O:8].[CH2:26](N(CC)CC)C.ClC(O[CH2:37][CH:38]([CH3:40])[CH3:39])=O.OC1C=C[C:45]([CH:46]=[N:47][NH:48][C:49]([NH2:51])=[O:50])=CC=1>CC(C)=O.N1C=CC=CC=1>[N:47](=[C:46]1[CH:26]=[CH:37][C:38]([CH3:39])=[C:40]([O:8][C:7](=[O:9])[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]2[S:1][C@H:12]3[CH2:13][C@@H:14]([OH:25])[C@H:15](/[CH:16]=[CH:17]/[C@@H:18]([OH:24])[CH2:19][CH2:20][CH2:21][CH2:22][CH3:23])[C@H:11]3[CH2:10]2)[CH2:45]1)[NH:48][C:49]([NH2:51])=[O:50]Komponenten
7
Edukt 4
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 2
Reaktionsbedingungen
- Temperatur
- 0 °C
Versuchsvorschrift
To a solution of 98 mg of (13E)-(6RS,9α,11α,15S)-6,9-epithio-11,15-dihydroxyprost-13-enoic acid (prepared as described in Example 2) and 52 μl of triethylamine in 3 ml of acetone was added 49 μl of isobutyl chloroformate at 0° C., and the mixture was stirred at 0° C. for 30 minutes. To it were added 1.4 ml of pyridine and 202 mg of 4-hydroxybenzaldehyde semicarbazone at ambient temperature, and the mixture was stirred at room temperature for 5 hours. The reaction mixture was concentrated under reduced pressure. The residue was purified by recrystallization from acetonitrile to give 29.5 mg of the title compound having the following physical characteristics: melting point: 90°-91° C.;
Aufarbeitung
- stirringthe mixture was stirred at room temperature for 5 hours
- concentrationThe reaction mixture was concentrated under reduced pressure
- customThe residue was purified by recrystallization from acetonitrile
Quellen und Nachweise
- ORD-Eintrag
- ord-7817aae2d3c5454cabe4ec4bbb21c11c
- Quelldatensatz
- uspto-grants-1983_01
- Patentnummer
- US04367237
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