p-Toluenesulfonic acid → HCID 86741215, Verbindung
Reaktionsgleichung
[CH2:1]([N:8]1[C@H:12]2[CH2:13][S:14][C:15](O)([CH2:16][CH2:17][CH2:18][CH2:19][C:20]34[CH2:29][CH:24]5[CH2:25][CH:26]([O:28][CH:22]([O:23]5)[O:21]3)[CH2:27]4)[C@H:11]2[N:10]([CH2:31][C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)[C:9]1=[O:38])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C1(C)C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1>[CH2:1]([N:8]1[C@H:12]2[CH2:13][S:14][C:15](=[CH:16][CH2:17][CH2:18][CH2:19][C:20]34[CH2:29][CH:24]5[CH2:25][CH:26]([O:28][CH:22]([O:23]5)[O:21]3)[CH2:27]4)[C@H:11]2[N:10]([CH2:31][C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)[C:9]1=[O:38])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1Komponenten
4
Edukt 2
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Versuchsvorschrift
910 mg (1.68 mmol) of cis-1,3-dibenzyl-4-hydroxy-4-(4-(2,4,10-trioxaadamantyl)-butyl)-hexahydro-1H-thieno[3,4-d]imidazol-2-one (prepared in accordance with Example 1) are dissolved in 50 ml of toluene and the solution is treated with 20 mg of p-toluenesulphonic acid. The solution is heated to boiling and 20 ml of toluene are distilled off within 1 hour. Thereafter, the solution is evaporated to dryness. The residue remaining is chromatographed on silica gel. Elution with toluene, toluene/ethyl acetate (9:1) and (8:2) gives 839 mg (96% of theory) of cis-1,3-dibenzyl-4-(4-(2,4,10-trioxaadamantyl)-butylidene)-hexahydro-1H-thieno[3,4-d]imidazol-2-one in the form of a light brown oil which solidifies upon drying.