p-Toluenesulfonic acid monohydrate → (S)-3-{[4-(4-Acetyl-3-hydroxy-2-propyl-phenylsulfanylmethyl)-phenyl]-hydroxy-methyl}-benzonitrile
Reaction equation
O.C1(C)C=CC(S(O)(=O)=O)=CC=1.[C:13]([C:16]1[CH:21]=[CH:20][C:19]([S:22][CH2:23][C:24]2[CH:29]=[CH:28][C:27]([C@H:30]([O:39]C3CCCCO3)[C:31]3[CH:32]=[C:33]([CH:36]=[CH:37][CH:38]=3)[C:34]#[N:35])=[CH:26][CH:25]=2)=[C:18]([CH2:46][CH2:47][CH3:48])[C:17]=1[OH:49])(=[O:15])[CH3:14]>CO>[C:13]([C:16]1[CH:21]=[CH:20][C:19]([S:22][CH2:23][C:24]2[CH:25]=[CH:26][C:27]([C@H:30]([OH:39])[C:31]3[CH:32]=[C:33]([CH:36]=[CH:37][CH:38]=3)[C:34]#[N:35])=[CH:28][CH:29]=2)=[C:18]([CH2:46][CH2:47][CH3:48])[C:17]=1[OH:49])(=[O:15])[CH3:14]Participants
4
Procedure
Add p-toluenesulfonic acid monohydrate (78 mg, 0.41 mmol) to a solution of (S)-3-[[4-(4-Acetyl-3-hydroxy-2-propyl-phenylsulfanylmethyl)-phenyl]-(tetrahydro-pyran-2-yloxy)-methyl]-benzonitrile (177 mg, 0.34 mmol) in methanol (5 ml) at room temperature. Stir the mixture for 1.5 hours, concentrate, and dissolve the residue in ethyl acetate (25 ml) and saturated aqueous sodium bicarbonate (35 ml). Wash the organic layer with saturated aqueous sodium bicarbonate, brine, dry over sodium sulfate and concentrate. Purify the crude product via silica chromatography eluting with 1:2 ethyl acetate:hexanes to give the title compound (122 mg, 84%). MS (m/z) 430 (M−H).