Salmeterol → Salmeterol 4-phenylcinnamate

HRID 2220126Notes

Reaction equation

HRID 2220126 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]=1

Participants

4

Reactant 2

HCID 5152SalmeterolHCID 254923-(4-Phenylphenyl)prop-2-enoic acid

Product 1

HCID 86760723Salmeterol 4-phenylcinnamateYield 1,226.2%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

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

Workup

  1. temperatureto cool
  2. filtrationThe suspension is filtered
  3. washthe precipitate is washed with ethyl acetate and tert-butylmethylether
  4. customdried in vacuo at 25° C.-30° C

Sources & evidence

ORD record
ord-1592578a693f4b61a603ac9d25977977
Source dataset
uspto-grants-2008_08
Patent number
US07417051B2

Reaction notes

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