Salmeterol → Salmeterol 4-phenylcinnamate
Reaction equation
[C:1]1([C:7]2[CH:17]=[CH:16][C:10]([CH:11]=[CH:12][C:13]([OH:15])=[O:14])=[CH:9][CH:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH:18]1[CH:19]=[CH:20][C:21]([CH2:24][CH2:25][CH2:26][CH2:27][O:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][NH:35][CH2:36][CH:37]([OH:47])[C:38]2[CH:39]=[CH:40][C:41]([OH:46])=[C:42]([CH2:44][OH:45])[CH:43]=2)=[CH:22][CH:23]=1>C(OCC)(=O)C>[CH:18]1[CH:19]=[CH:20][C:21]([CH2:24][CH2:25][CH2:26][CH2:27][O:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][NH:35][CH2:36][CH:37]([OH:47])[C:38]2[CH:39]=[CH:40][C:41]([OH:46])=[C:42]([CH2:44][OH:45])[CH:43]=2)=[CH:22][CH:23]=1.[C:1]1([C:7]2[CH:8]=[CH:9][C:10]([CH:11]=[CH:12][C:13]([O-:15])=[O:14])=[CH:16][CH:17]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
1.35 g (6 mmol) of 4-phenylcinnamic acid is dissolved by refluxing in 75 mL of ethyl acetate. To this solution is added a warm solution of 2.5 g (6 mmol) of salmeterol in 25 mL of ethyl acetate. The solution is allowed to cool and stirred for 16 hours at room temperature. The suspension is filtered, the precipitate is washed with ethyl acetate and tert-butylmethylether and dried in vacuo at 25° C.-30° C. 47 g of the title compound are obtained as a colorless solid. Melting point: 109° C. 2.2. Salmeterol-5-(2,4-difluorophenyl)salicylate Salt 2c