Piperidine → 2-[4-(4-phenoxyphenylthio)-N-CBZ-piperidin-4-yl]-acetic acid

Reaktionsgleichung

[O:1]([C:8]1[CH:13]=[CH:12][C:11]([SH:14])=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:15]([CH:18]=[C:19]1[CH2:24][CH2:23][N:22]([C:25]([O:27][CH2:28][C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)=[O:26])[CH2:21][CH2:20]1)([OH:17])=[O:16].N1CCCCC1>>[O:1]([C:8]1[CH:13]=[CH:12][C:11]([S:14][C:19]2([CH2:18][C:15]([OH:17])=[O:16])[CH2:24][CH2:23][N:22]([C:25]([O:27][CH2:28][C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=3)=[O:26])[CH2:21][CH2:20]2)=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Komponenten

Edukt 3

HCID 8082Piperidine

HCID 27603544-Phenoxythiophenol

HCID 212243161-Cbz-Piperidin-4-ylidene-acetic acid

Produkt 1

HCID 212241102-[4-(4-phenoxyphenylthio)-N-CBZ-piperidin-4-yl]-acetic acid

Versuchsvorschrift

4-Phenoxythiophenol (7.4 g, 36.3 mmol), 4-carboxymethylene-N-CBZ-piperidine (10 g, 36.3 mmol) and piperidine (1.8 ml, 36.3 mmol) were stirred overnight at 100-110° C. in a sealed flask. After cooling, the crude reaction mixture was partitioned between ethyl acetate and 1N hydrochloric acid, the organic layer was washed with brine, dried over magnesium sulfate, filtered, and concentrated in vacuo to give a yellow solid. The solid was triturated in 1:1 (v/v) ethyl ether/hexane (500 ml) to give 2-[4-(4-phenoxyphenylthio)-N-CBZ-piperidin-4-yl]-acetic acid as a white solid.