Acetic Anhydride → Ralaniten Acetate

Reaction equation

C(O[C:5](=[O:7])[CH3:6])(=O)C.[Cl:8][CH2:9][C@@H:10]([OH:34])[CH2:11][O:12][C:13]1[CH:18]=[CH:17][C:16]([C:19]([C:22]2[CH:33]=[CH:32][C:25]([O:26][CH2:27][C@H:28]([OH:31])[CH2:29][OH:30])=[CH:24][CH:23]=2)([CH3:21])[CH3:20])=[CH:15][CH:14]=1>CN(C1C=CN=CC=1)C.N1C=CC=CC=1>[C:11]([O:30][CH2:29][C@@H:28]([O:31][C:5](=[O:7])[CH3:6])[CH2:27][O:26][C:25]1[CH:24]=[CH:23][C:22]([C:19]([C:16]2[CH:15]=[CH:14][C:13]([O:12][CH2:11][C@H:10]([O:34][C:25](=[O:26])[CH3:24])[CH2:9][Cl:8])=[CH:18][CH:17]=2)([CH3:21])[CH3:20])=[CH:33][CH:32]=1)(=[O:12])[CH3:10]

Participants

Procedure

Acetic Anhydride (4.3 g, 41.7 mmol) was added to a solution of (R)-3-(4-(2-(4-((S)-3-chloro-2-hydroxypropoxy)phenyl)propan-2-yl)phenoxy)propane-1,2-diol (2.8 g, 6.95 mmol) and DMAP (30 mg, 0.25 mmol) in anhydrous pyridine (24 mL) in a water bath. The resulting solution was stirred overnight. The pyridine was removed under reduced pressure and the residue was diluted with ethyl acetate (50 mL), washed subsequently with water (2×40 mL), then cold aqueous 1M HCl (40 mL), saturated NaHCO3 (40 mL) and water (40 mL). The organic layer was dried over Mg2SO4, filtered and concentrated to give light yellow oil. The crude product was purified by column chromatography (eluent: 5% ethyl acetate in hexane to 20% ethyl acetate in hexane) to afford the title compound (3.30 g, 91.5% yield) as a colorless viscous oil.